Name: 136030-33-6|(S)-2-(((9H-Fluoren-9-yl)methoxy)carbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid|98%
Brand: Ambeed
SKU: A403656
Price: 5.0 USD
Availability: InStock
Rating: 93 (27 reviews)

1
[ 71989-18-9 ]
[ 136030-33-6 ]
[ 99953-00-1 ]
[ 76-05-1 ]
[ 845255-75-6 ]
(S)-4-({(S)-2-[(S)-2-Amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionyl]-1,2,3,4-tetrahydro-isoquinoline-3-carbonyl}-amino)-4-[(S)-1-carbamoyl-2-(6-dimethylamino-1,3-dioxo-1,3-dihydro-benzo[f]isoindol-2-yl)-ethylcarbamoyl]-butyric acid; compound with trifluoro-acetic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3653 - 3658

2
[ 71989-26-9 ]
[ 136030-33-6 ]
C₆H₅CH₂CH(NH₂)C(O)O-2-ClTrt resin [ No CAS ]
C₅₀H₆₀N₈O₆ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 4731 - 4739

3
[ 119831-72-0 ]
[ 136030-33-6 ]
C₆H₅CH₂CH(NH₂)C(O)O-2-ClTrt resin [ No CAS ]
C₅₀H₅₈N₁₀O₈ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 4731 - 4739

4
[ 71989-18-9 ]
[ 136030-33-6 ]
[ 99953-00-1 ]
[ 88574-06-5 ]
[ 76-05-1 ]
Fmoc-α-amino-β-(6-N,N-dimethylamino naphthalimide)propanoic acid [ No CAS ]
C₄₉H₅₈N₈O₁₀*2C₂HF₃O₂ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3653 - 3658

5
[ 71989-26-9 ]
[ 136030-33-6 ]
(N-Boc-indol-3-yl)CH₂CH(NH₂)C(O)O-2-ClTrt resin [ No CAS ]
C₅₄H₆₂N₁₀O₆ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 4731 - 4739

6
[ 68858-20-8 ]
[ 35661-60-0 ]
[ 35661-39-3 ]
[ 136030-33-6 ]
Fmoc-Tyr(t-Bu)-OHN-Fmoc-3-aminomethylbenzoic acid [ No CAS ]
βALA-G(ΨCH2NH)Tic-(3-aminomethylbenzoic acid)-LTV [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 1598 - 1609

7
[ 136030-33-6 ]
[ 839720-27-3 ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 56 - 70

8
[ 136030-33-6 ]
[ 839720-28-4 ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 56 - 70

9
[ 136030-33-6 ]
L-N-[3-[[4-[(3-aminopropyl)amino]butyl]amino]propyl]-2-(1-oxobutyl)isoquinoline-3-carboxylamide tris(trifluoroacetate) [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 56 - 70

10
[ 136030-33-6 ]
3-[3-(tert-butoxycarbonyl-{4-[tert-butoxycarbonyl-(3-tert-butoxycarbonylamino-propyl)-amino]-butyl}-amino)-propylcarbamoyl]-3,4-dihydro-1H-isoquinoline-2-carboxylic acid 9H-fluoren-9-ylmethyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 56 - 70

11
[ 136030-33-6 ]
[ 166168-89-4 ]

Reference： [1]Il Farmaco,1999,vol. 54,p. 785 - 790

12
[ 136030-33-6 ]
[ 166168-91-8 ]

Reference： [1]Il Farmaco,1999,vol. 54,p. 785 - 790

13
[ 136030-33-6 ]
[ 166168-90-7 ]

Reference： [1]Il Farmaco,1999,vol. 54,p. 785 - 790

14
[ 136030-33-6 ]
(S)-2-({(S)-2-[(S)-2-(4-Chloro-2-hydroxy-benzoylamino)-3-methyl-butyryl]-1,2,3,4-tetrahydro-isoquinoline-3-carbonyl}-amino)-4-methylsulfanyl-butyric acid methyl ester [ No CAS ]

Reference： [1]Il Farmaco,1999,vol. 54,p. 785 - 790

15
[ 136030-33-6 ]
(S)-2-({(S)-2-[(S)-2-(5-Bromo-2-hydroxy-benzoylamino)-3-methyl-butyryl]-1,2,3,4-tetrahydro-isoquinoline-3-carbonyl}-amino)-4-methylsulfanyl-butyric acid [ No CAS ]

Reference： [1]Il Farmaco,1999,vol. 54,p. 785 - 790

16
[ 136030-33-6 ]
(S)-2-({(S)-2-[(S)-2-(4-Chloro-2-hydroxy-benzoylamino)-3-methyl-butyryl]-1,2,3,4-tetrahydro-isoquinoline-3-carbonyl}-amino)-4-methylsulfanyl-butyric acid [ No CAS ]

Reference： [1]Il Farmaco,1999,vol. 54,p. 785 - 790

17
[ 136030-33-6 ]
(S)-2-({(S)-2-[(S)-2-(5-Bromo-2-hydroxy-benzoylamino)-3-methyl-butyryl]-1,2,3,4-tetrahydro-isoquinoline-3-carbonyl}-amino)-4-methylsulfanyl-butyric acid methyl ester [ No CAS ]

Reference： [1]Il Farmaco,1999,vol. 54,p. 785 - 790

18
C₃₀H₃₅N₄O₃Pol [ No CAS ]
[ 136030-33-6 ]
C₅₅H₅₄N₅O₆Pol [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 4881 - 4889

19
C₂₆H₂₉N₂O₂Pol [ No CAS ]
[ 136030-33-6 ]
C₅₁H₄₈N₃O₅Pol [ No CAS ]

Reference： [1]Organic Letters,2009,vol. 11,p. 2479 - 2482

20
Fmoc-Arg(Pbf) [ No CAS ]
[ 103-72-0 ]
[ 136030-33-6 ]
[ 96-32-2 ]
[ 134-96-3 ]
[ 1194838-52-2 ]

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 7065 - 7074

21
[ 68858-20-8 ]
[ 35661-40-6 ]
[ 71989-38-3 ]
[ 71989-26-9 ]
[ 103213-32-7 ]
[ 136030-33-6 ]
[ 143824-78-6 ]
Fmoc-S-trityl penicillamine [ No CAS ]
C₅₈H₇₄N₁₀O₁₀S₂ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 3927 - 3940

22
[ 68858-20-8 ]
[ 35661-40-6 ]
[ 71989-38-3 ]
[ 103213-32-7 ]
[ 109425-55-0 ]
[ 136030-33-6 ]
1-tert-butoxycarbonyl-N-[(9-fluorenyl)methoxycarbonyl]-D-tryptophan [ No CAS ]
Fmoc-S-trityl penicillamine [ No CAS ]
C₅₇H₇₂N₁₀O₁₀S₂ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 3927 - 3940

23
knorr amide resin [ No CAS ]
[ 29022-11-5 ]
[ 68858-20-8 ]
[ 35661-60-0 ]
[ 71989-38-3 ]
[ 71989-26-9 ]
[ 103213-32-7 ]
[ 136030-33-6 ]
[ 109425-51-6 ]
[ 109425-56-1 ]
UGVCCGYKLCH[TIK]C-NH₂; U = L-pyroglutamic acid; [TIK] = 1,2,3,4-L-tetrahydroisoquinoline-3-carboxylic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 6991 - 7002

24
[ 29022-11-5 ]
[ 35661-40-6 ]
[ 108-24-7 ]
[ 105047-45-8 ]
[ 136030-33-6 ]
1‐fluorenylmethoxycarbonyl-(2S,3aS,7aS)‐octahydroindole‐2‐carboxylic acid [ No CAS ]
Ac-GF-Tic-Oic-GK-Tic-Oic-GF-Tic-Oic-GK-Tic-KKKK-CONH₂ [ No CAS ]

Reference： [1]Chemistry and Physics of Lipids,2010,vol. 163,p. 488 - 497

25
[ 29022-11-5 ]
[ 35661-60-0 ]
[ 71989-14-5 ]
[ 71989-38-3 ]
[ 136030-33-6 ]
[ 1273019-50-3 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2011,vol. 59,p. 2478 - 2485

26
[ 29022-11-5 ]
[ 35661-60-0 ]
[ 71989-14-5 ]
[ 71989-38-3 ]
[ 136030-33-6 ]
[ 1273019-51-4 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2011,vol. 59,p. 2478 - 2485

27
[ 2459-05-4 ]
C₂₁H₂₀N₃O₅Pol [ No CAS ]
[ 71989-31-6 ]
[ 108-24-7 ]
[ 136030-33-6 ]
[ 1312616-96-8 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: All aza-peptidyl inhibitors and probes were synthesized by following the previously reported procedures 1, 2 with slight modifications. Fmoc protecting groups from Rink SS resin (0.75 mmol/g) were removed by treatment with 20% piperidine in DMF for 15 min, followed by three washes with DMF. A 1.2 M solution of bromoacetic acid (10 eq) in NMP and DIC (10 eq) were added to the resin. The resin was shaken 1.5 hrs and washed three times. A solution of Mono-Fmoc protected hydrazide (3 eq) in NMP was added and shaken overnight. Resin loading was determined by Fmoc-quantification (0.2-0.3 mmol/g). A 0.5M solution of N-Fmoc-protected amino acid (3 eq.) and HOBt (3 eq.) in DMF and DIC (3 eq.) were added to the resin. The resin was shaken 1.5-2hrs. For each of the following steps, Fmoc-deprotection and coupling reactions were repeated as described above. Capping of N-terminal amine was achieved by shaking the resin with a 0.5 M solution of acetic anhydride (5 eq.) and DIEA (5 eq.) in DMF for 5 min.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 1340 - 1343

28
C₂₁H₂₂NO₄Pol [ No CAS ]
[ 304697-38-9 ]
[ 29022-11-5 ]
[ 57618-17-4 ]
[ 71989-14-5 ]
[ 71989-18-9 ]
[ 71989-26-9 ]
[ 71989-35-0 ]
[ 136030-33-6 ]
[ 71989-31-6 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
C₁₁₀H₁₅₆N₁₈O₂₆S [ No CAS ]

Reference： [1]Amino Acids,2012,vol. 43,p. 289 - 298

29
[ 503-74-2 ]
[ 1414927-98-2 ]
[ 136030-33-6 ]
[ 1414928-01-0 ]

Yield	Reaction Conditions	Operation in experiment
1.9 mg		General procedure: The chlorosilyl resin was swollen in dry DCM (20 mL) under argon atmosphere. A solution of imidazole (1.16 g, 17.0 mmol) and diol 5 (10.7 g, 16.8 mmol) in DCM (20 mL) was subsequently added. The mixture was vortexed overnight at room temperature using a Burrell wrist-action shaker. The loaded resin was washed with DCM (3 × 75 mL) and dried overnight under vacuum to provide 7.3 g of resin 6 (loading of 0.40 mmol/g). IR (KBr): nu 3442 (OH, alcohol), 1702 (C=O, carbamate) cm-1. The free diol 5 (8.7 g) was easily recovered after flash chromatography using EtOAc/hexanes (1:1) as eluent. A solution of piperidine in DCM (20% v/v) (70 mL) was added to resin 6 (7.3 g, 0.4 mmol/g) and the suspension was vortexed using a Burrell wrist-action shaker for 1 h at room temperature. The resin was then filtered and washed successively with DCM (5 × 75 mL) and MeOH (5 × 75 mL), and finally dried overnight to provide 6.5 g of Fmoc deprotected resin. The resin was divided into portions (1.80 g, 0.4 mmol/g in a 50 mL peptide flask). To each portion was added a solution of the appropriate amino acid (Fmoc-l-proline-OH (2.5 g, 7.5 mmol), Fmoc-d-proline-OH (2.5 g, 7.5 mmol), Fmoc-l-phenylalanine-OH (2.9 g, 7.5 mmol), Fmoc-d-phenylalanine-OH (2.9 g, 7.5 mmol) or Fmoc-l-tetrahydro-isoquinoline-3-carboxylic acid (3.0 g, 7.5 mmol), benzotriazole-yl-oxy-tris-pyrrolidinophosphonium hexafluorophosphate (PyBOP) (3.9 g, 7.5 mmol) and N-hydroxybenzotriazole (HOBt) (1.0 g, 7.5 mmol) in DMF (25 mL) under argon atmosphere. Diisopropylethylamine (DIPEA) (2.6 mL, 15 mmol) was added to the suspensions and the peptide flasks were vortexed with a Burrell wrist-action shaker for 5 h at room temperature. The resins were then filtered and washed successively with DCM (5 × 25 mL) and MeOH (5 × 25 mL), and finally dried overnight to give the resins 7. The coupling reaction was repeated a second time in each case in order to ensure complete coupling. A solution of piperidine in DCM (20% v/v) (70 mL) was added to resin 6 (7.3 g, 0.4 mmol/g) and the suspension was vortexed using a Burrell wrist-action shaker for 1 h at room temperature. The resin was then filtered and washed successively with DCM (5 × 75 mL) and MeOH (5 × 75 mL), and finally dried overnight to provide 6.5 g of Fmoc deprotected resin. The resin was divided into portions (1.80 g, 0.4 mmol/g in a 50 mL peptide flask). To each portion was added a solution of the appropriate amino acid (Fmoc-l-proline-OH (2.5 g, 7.5 mmol), Fmoc-d-proline-OH (2.5 g, 7.5 mmol), Fmoc-l-phenylalanine-OH (2.9 g, 7.5 mmol), Fmoc-d-phenylalanine-OH (2.9 g, 7.5 mmol) or Fmoc-l-tetrahydro-isoquinoline-3-carboxylic acid (3.0 g, 7.5 mmol), benzotriazole-yl-oxy-tris-pyrrolidinophosphonium hexafluorophosphate (PyBOP) (3.9 g, 7.5 mmol) and N-hydroxybenzotriazole (HOBt) (1.0 g, 7.5 mmol) in DMF (25 mL) under argon atmosphere. Diisopropylethylamine (DIPEA) (2.6 mL, 15 mmol) was added to the suspensions and the peptide flasks were vortexed with a Burrell wrist-action shaker for 5 h at room temperature. The resins were then filtered and washed successively with DCM (5 × 25 mL) and MeOH (5 × 25 mL), and finally dried overnight to give the resins 7. The coupling reaction was repeated a second time in each case in order to ensure complete coupling. To each of the resin-bound derivatives 8 was added 2 mL of an acid solution of 2 M methanolic HCl (AcCl + MeOH) in DCM (20:80, v/v) and the resulting suspensions were vortexed at 600 rpm for 1 h. DCM (1 mL) was added and the suspensions were filtered and the recovered filtrate was neutralized with 0.5 mL of 10% aqueous NaHCO3 (pH 8). The biphasic solution was filtered using a phase separator syringe (Biotage) and the resulting organic solution evaporated under reduced pressure. The 12 (3 × 4) crude amide compounds of library A (Table 2 ) were purified by filtration over a silica gel plug (10 mL) using EtOAc/hexanes (1:1) (15 mL) and then EtOAc (20 mL). In another experiment, the 28 (4 × 7) amide compounds of library B (Table 3 ) were evaporated to dryness and judged sufficiently pure by TLC and 1H NMR analyses for direct screening on HL-60 cells. All members of libraries A and B were analyzed by TLC, 1H NMR and LRMS.

Reference： [1]Steroids,2012,vol. 77,p. 1403 - 1418

30
[ 140-77-2 ]
[ 1414927-98-2 ]
[ 136030-33-6 ]
[ 1414928-04-3 ]

Yield	Reaction Conditions	Operation in experiment
1.4 mg		General procedure: The chlorosilyl resin was swollen in dry DCM (20 mL) under argon atmosphere. A solution of imidazole (1.16 g, 17.0 mmol) and diol 5 (10.7 g, 16.8 mmol) in DCM (20 mL) was subsequently added. The mixture was vortexed overnight at room temperature using a Burrell wrist-action shaker. The loaded resin was washed with DCM (3 × 75 mL) and dried overnight under vacuum to provide 7.3 g of resin 6 (loading of 0.40 mmol/g). IR (KBr): nu 3442 (OH, alcohol), 1702 (C=O, carbamate) cm-1. The free diol 5 (8.7 g) was easily recovered after flash chromatography using EtOAc/hexanes (1:1) as eluent. A solution of piperidine in DCM (20% v/v) (70 mL) was added to resin 6 (7.3 g, 0.4 mmol/g) and the suspension was vortexed using a Burrell wrist-action shaker for 1 h at room temperature. The resin was then filtered and washed successively with DCM (5 × 75 mL) and MeOH (5 × 75 mL), and finally dried overnight to provide 6.5 g of Fmoc deprotected resin. The resin was divided into portions (1.80 g, 0.4 mmol/g in a 50 mL peptide flask). To each portion was added a solution of the appropriate amino acid (Fmoc-l-proline-OH (2.5 g, 7.5 mmol), Fmoc-d-proline-OH (2.5 g, 7.5 mmol), Fmoc-l-phenylalanine-OH (2.9 g, 7.5 mmol), Fmoc-d-phenylalanine-OH (2.9 g, 7.5 mmol) or Fmoc-l-tetrahydro-isoquinoline-3-carboxylic acid (3.0 g, 7.5 mmol), benzotriazole-yl-oxy-tris-pyrrolidinophosphonium hexafluorophosphate (PyBOP) (3.9 g, 7.5 mmol) and N-hydroxybenzotriazole (HOBt) (1.0 g, 7.5 mmol) in DMF (25 mL) under argon atmosphere. Diisopropylethylamine (DIPEA) (2.6 mL, 15 mmol) was added to the suspensions and the peptide flasks were vortexed with a Burrell wrist-action shaker for 5 h at room temperature. The resins were then filtered and washed successively with DCM (5 × 25 mL) and MeOH (5 × 25 mL), and finally dried overnight to give the resins 7. The coupling reaction was repeated a second time in each case in order to ensure complete coupling. A solution of piperidine in DCM (20% v/v) (70 mL) was added to resin 6 (7.3 g, 0.4 mmol/g) and the suspension was vortexed using a Burrell wrist-action shaker for 1 h at room temperature. The resin was then filtered and washed successively with DCM (5 × 75 mL) and MeOH (5 × 75 mL), and finally dried overnight to provide 6.5 g of Fmoc deprotected resin. The resin was divided into portions (1.80 g, 0.4 mmol/g in a 50 mL peptide flask). To each portion was added a solution of the appropriate amino acid (Fmoc-l-proline-OH (2.5 g, 7.5 mmol), Fmoc-d-proline-OH (2.5 g, 7.5 mmol), Fmoc-l-phenylalanine-OH (2.9 g, 7.5 mmol), Fmoc-d-phenylalanine-OH (2.9 g, 7.5 mmol) or Fmoc-l-tetrahydro-isoquinoline-3-carboxylic acid (3.0 g, 7.5 mmol), benzotriazole-yl-oxy-tris-pyrrolidinophosphonium hexafluorophosphate (PyBOP) (3.9 g, 7.5 mmol) and N-hydroxybenzotriazole (HOBt) (1.0 g, 7.5 mmol) in DMF (25 mL) under argon atmosphere. Diisopropylethylamine (DIPEA) (2.6 mL, 15 mmol) was added to the suspensions and the peptide flasks were vortexed with a Burrell wrist-action shaker for 5 h at room temperature. The resins were then filtered and washed successively with DCM (5 × 25 mL) and MeOH (5 × 25 mL), and finally dried overnight to give the resins 7. The coupling reaction was repeated a second time in each case in order to ensure complete coupling. To each of the resin-bound derivatives 8 was added 2 mL of an acid solution of 2 M methanolic HCl (AcCl + MeOH) in DCM (20:80, v/v) and the resulting suspensions were vortexed at 600 rpm for 1 h. DCM (1 mL) was added and the suspensions were filtered and the recovered filtrate was neutralized with 0.5 mL of 10% aqueous NaHCO3 (pH 8). The biphasic solution was filtered using a phase separator syringe (Biotage) and the resulting organic solution evaporated under reduced pressure. The 12 (3 × 4) crude amide compounds of library A (Table 2 ) were purified by filtration over a silica gel plug (10 mL) using EtOAc/hexanes (1:1) (15 mL) and then EtOAc (20 mL). In another experiment, the 28 (4 × 7) amide compounds of library B (Table 3 ) were evaporated to dryness and judged sufficiently pure by TLC and 1H NMR analyses for direct screening on HL-60 cells. All members of libraries A and B were analyzed by TLC, 1H NMR and LRMS.

Reference： [1]Steroids,2012,vol. 77,p. 1403 - 1418

31
[ 1414927-98-2 ]
[ 136030-33-6 ]
[ 98-89-5 ]
[ 1414928-07-6 ]

Yield	Reaction Conditions	Operation in experiment
1.2 mg		General procedure: The chlorosilyl resin was swollen in dry DCM (20 mL) under argon atmosphere. A solution of imidazole (1.16 g, 17.0 mmol) and diol 5 (10.7 g, 16.8 mmol) in DCM (20 mL) was subsequently added. The mixture was vortexed overnight at room temperature using a Burrell wrist-action shaker. The loaded resin was washed with DCM (3 × 75 mL) and dried overnight under vacuum to provide 7.3 g of resin 6 (loading of 0.40 mmol/g). IR (KBr): nu 3442 (OH, alcohol), 1702 (C=O, carbamate) cm-1. The free diol 5 (8.7 g) was easily recovered after flash chromatography using EtOAc/hexanes (1:1) as eluent. A solution of piperidine in DCM (20% v/v) (70 mL) was added to resin 6 (7.3 g, 0.4 mmol/g) and the suspension was vortexed using a Burrell wrist-action shaker for 1 h at room temperature. The resin was then filtered and washed successively with DCM (5 × 75 mL) and MeOH (5 × 75 mL), and finally dried overnight to provide 6.5 g of Fmoc deprotected resin. The resin was divided into portions (1.80 g, 0.4 mmol/g in a 50 mL peptide flask). To each portion was added a solution of the appropriate amino acid (Fmoc-l-proline-OH (2.5 g, 7.5 mmol), Fmoc-d-proline-OH (2.5 g, 7.5 mmol), Fmoc-l-phenylalanine-OH (2.9 g, 7.5 mmol), Fmoc-d-phenylalanine-OH (2.9 g, 7.5 mmol) or Fmoc-l-tetrahydro-isoquinoline-3-carboxylic acid (3.0 g, 7.5 mmol), benzotriazole-yl-oxy-tris-pyrrolidinophosphonium hexafluorophosphate (PyBOP) (3.9 g, 7.5 mmol) and N-hydroxybenzotriazole (HOBt) (1.0 g, 7.5 mmol) in DMF (25 mL) under argon atmosphere. Diisopropylethylamine (DIPEA) (2.6 mL, 15 mmol) was added to the suspensions and the peptide flasks were vortexed with a Burrell wrist-action shaker for 5 h at room temperature. The resins were then filtered and washed successively with DCM (5 × 25 mL) and MeOH (5 × 25 mL), and finally dried overnight to give the resins 7. The coupling reaction was repeated a second time in each case in order to ensure complete coupling. A solution of piperidine in DCM (20% v/v) (70 mL) was added to resin 6 (7.3 g, 0.4 mmol/g) and the suspension was vortexed using a Burrell wrist-action shaker for 1 h at room temperature. The resin was then filtered and washed successively with DCM (5 × 75 mL) and MeOH (5 × 75 mL), and finally dried overnight to provide 6.5 g of Fmoc deprotected resin. The resin was divided into portions (1.80 g, 0.4 mmol/g in a 50 mL peptide flask). To each portion was added a solution of the appropriate amino acid (Fmoc-l-proline-OH (2.5 g, 7.5 mmol), Fmoc-d-proline-OH (2.5 g, 7.5 mmol), Fmoc-l-phenylalanine-OH (2.9 g, 7.5 mmol), Fmoc-d-phenylalanine-OH (2.9 g, 7.5 mmol) or Fmoc-l-tetrahydro-isoquinoline-3-carboxylic acid (3.0 g, 7.5 mmol), benzotriazole-yl-oxy-tris-pyrrolidinophosphonium hexafluorophosphate (PyBOP) (3.9 g, 7.5 mmol) and N-hydroxybenzotriazole (HOBt) (1.0 g, 7.5 mmol) in DMF (25 mL) under argon atmosphere. Diisopropylethylamine (DIPEA) (2.6 mL, 15 mmol) was added to the suspensions and the peptide flasks were vortexed with a Burrell wrist-action shaker for 5 h at room temperature. The resins were then filtered and washed successively with DCM (5 × 25 mL) and MeOH (5 × 25 mL), and finally dried overnight to give the resins 7. The coupling reaction was repeated a second time in each case in order to ensure complete coupling. To each of the resin-bound derivatives 8 was added 2 mL of an acid solution of 2 M methanolic HCl (AcCl + MeOH) in DCM (20:80, v/v) and the resulting suspensions were vortexed at 600 rpm for 1 h. DCM (1 mL) was added and the suspensions were filtered and the recovered filtrate was neutralized with 0.5 mL of 10% aqueous NaHCO3 (pH 8). The biphasic solution was filtered using a phase separator syringe (Biotage) and the resulting organic solution evaporated under reduced pressure. The 12 (3 × 4) crude amide compounds of library A (Table 2 ) were purified by filtration over a silica gel plug (10 mL) using EtOAc/hexanes (1:1) (15 mL) and then EtOAc (20 mL). In another experiment, the 28 (4 × 7) amide compounds of library B (Table 3 ) were evaporated to dryness and judged sufficiently pure by TLC and 1H NMR analyses for direct screening on HL-60 cells. All members of libraries A and B were analyzed by TLC, 1H NMR and LRMS.

Reference： [1]Steroids,2012,vol. 77,p. 1403 - 1418

32
[ 112-05-0 ]
[ 1414927-98-2 ]
[ 136030-33-6 ]
[ 1414928-10-1 ]

Yield	Reaction Conditions	Operation in experiment
2.1 mg		General procedure: The chlorosilyl resin was swollen in dry DCM (20 mL) under argon atmosphere. A solution of imidazole (1.16 g, 17.0 mmol) and diol 5 (10.7 g, 16.8 mmol) in DCM (20 mL) was subsequently added. The mixture was vortexed overnight at room temperature using a Burrell wrist-action shaker. The loaded resin was washed with DCM (3 × 75 mL) and dried overnight under vacuum to provide 7.3 g of resin 6 (loading of 0.40 mmol/g). IR (KBr): nu 3442 (OH, alcohol), 1702 (C=O, carbamate) cm-1. The free diol 5 (8.7 g) was easily recovered after flash chromatography using EtOAc/hexanes (1:1) as eluent. A solution of piperidine in DCM (20% v/v) (70 mL) was added to resin 6 (7.3 g, 0.4 mmol/g) and the suspension was vortexed using a Burrell wrist-action shaker for 1 h at room temperature. The resin was then filtered and washed successively with DCM (5 × 75 mL) and MeOH (5 × 75 mL), and finally dried overnight to provide 6.5 g of Fmoc deprotected resin. The resin was divided into portions (1.80 g, 0.4 mmol/g in a 50 mL peptide flask). To each portion was added a solution of the appropriate amino acid (Fmoc-l-proline-OH (2.5 g, 7.5 mmol), Fmoc-d-proline-OH (2.5 g, 7.5 mmol), Fmoc-l-phenylalanine-OH (2.9 g, 7.5 mmol), Fmoc-d-phenylalanine-OH (2.9 g, 7.5 mmol) or Fmoc-l-tetrahydro-isoquinoline-3-carboxylic acid (3.0 g, 7.5 mmol), benzotriazole-yl-oxy-tris-pyrrolidinophosphonium hexafluorophosphate (PyBOP) (3.9 g, 7.5 mmol) and N-hydroxybenzotriazole (HOBt) (1.0 g, 7.5 mmol) in DMF (25 mL) under argon atmosphere. Diisopropylethylamine (DIPEA) (2.6 mL, 15 mmol) was added to the suspensions and the peptide flasks were vortexed with a Burrell wrist-action shaker for 5 h at room temperature. The resins were then filtered and washed successively with DCM (5 × 25 mL) and MeOH (5 × 25 mL), and finally dried overnight to give the resins 7. The coupling reaction was repeated a second time in each case in order to ensure complete coupling. A solution of piperidine in DCM (20% v/v) (70 mL) was added to resin 6 (7.3 g, 0.4 mmol/g) and the suspension was vortexed using a Burrell wrist-action shaker for 1 h at room temperature. The resin was then filtered and washed successively with DCM (5 × 75 mL) and MeOH (5 × 75 mL), and finally dried overnight to provide 6.5 g of Fmoc deprotected resin. The resin was divided into portions (1.80 g, 0.4 mmol/g in a 50 mL peptide flask). To each portion was added a solution of the appropriate amino acid (Fmoc-l-proline-OH (2.5 g, 7.5 mmol), Fmoc-d-proline-OH (2.5 g, 7.5 mmol), Fmoc-l-phenylalanine-OH (2.9 g, 7.5 mmol), Fmoc-d-phenylalanine-OH (2.9 g, 7.5 mmol) or Fmoc-l-tetrahydro-isoquinoline-3-carboxylic acid (3.0 g, 7.5 mmol), benzotriazole-yl-oxy-tris-pyrrolidinophosphonium hexafluorophosphate (PyBOP) (3.9 g, 7.5 mmol) and N-hydroxybenzotriazole (HOBt) (1.0 g, 7.5 mmol) in DMF (25 mL) under argon atmosphere. Diisopropylethylamine (DIPEA) (2.6 mL, 15 mmol) was added to the suspensions and the peptide flasks were vortexed with a Burrell wrist-action shaker for 5 h at room temperature. The resins were then filtered and washed successively with DCM (5 × 25 mL) and MeOH (5 × 25 mL), and finally dried overnight to give the resins 7. The coupling reaction was repeated a second time in each case in order to ensure complete coupling. To each of the resin-bound derivatives 8 was added 2 mL of an acid solution of 2 M methanolic HCl (AcCl + MeOH) in DCM (20:80, v/v) and the resulting suspensions were vortexed at 600 rpm for 1 h. DCM (1 mL) was added and the suspensions were filtered and the recovered filtrate was neutralized with 0.5 mL of 10% aqueous NaHCO3 (pH 8). The biphasic solution was filtered using a phase separator syringe (Biotage) and the resulting organic solution evaporated under reduced pressure. The 12 (3 × 4) crude amide compounds of library A (Table 2 ) were purified by filtration over a silica gel plug (10 mL) using EtOAc/hexanes (1:1) (15 mL) and then EtOAc (20 mL). In another experiment, the 28 (4 × 7) amide compounds of library B (Table 3 ) were evaporated to dryness and judged sufficiently pure by TLC and 1H NMR analyses for direct screening on HL-60 cells. All members of libraries A and B were analyzed by TLC, 1H NMR and LRMS.

Reference： [1]Steroids,2012,vol. 77,p. 1403 - 1418

33
[ 1443251-62-4 ]
[ 136030-33-6 ]
3-isobutyl-3-phenyl-5-((S)-1,2,3,4-tetrahydroisoquinoline-3-carbonyl)-4,5,6,7-tetrahydrofuro[3,4-c]pyridin-1(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%		To a solution of (S)-2-(((9H-fluoren-9- yl)methoxy)carbonyl)- l,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (147 mg, 0.369 mmol), 3-isobutyl-3-phenyl-4,5,6,7-tetrahydrofuro[3,4-c]pyridin- l(3H)-one (50 mg, 0.184 mmol), and N,N'-diisopropylethylamine (112 mg, 0.870 mmol) in THF (5 mL) was added BOP reagent (144 mg, 0.326 mmol) and the mixture was stirred at room temperature for 16 hours. The reaction mixture was concentrated to dryness, re-dissolved in 20% piperidine in DMF (5 mL), and stirred at room temperature for 1 hour. The crude reaction mixture was concentrated and purified by column chromatography (12 g, Si02, 0 to 100% ethyl acetate in hexanes) to provide 3-isobutyl-3-phenyl-5-((S)- l,2,3,4-tetrahydroisoquinoline-3-carbonyl)- 4,5,6,7-tetrahydrofuro[3,4-c]pyridin- l(3H)-one (54 mg, 68%) as a mixture of diastereoisomers in form of white solid: 1H NMR (300 MHz, CHLOROFORM- ) delta ppm 0.81 - 1.01 (m, 6 H), 1.59 - 1.74 (m, 1 H), 1.75 - 1.88 (m, 1 H), 2.26 - 2.52 (m, 3 H), 2.71 - 2.85 (m, 1 H), 2.87 - 3.10 (m, 1 H), 3.37 - 3.72 (m, 2 H), 3.76 - 3.99 (m, 2 H), 4.00 - 4.15 (m, 3 H), 4.62 - 4.86 (m, 1 H), 7.01 - 7.22 (m, 4 H), 7.28 - 7.45 (m, 5 H); MS m/z 431 (M+H) +, 429 (M-H)".

Reference： [1]Patent: WO2013/86200,2013,A1 .Location in patent: Paragraph 0113

34
[ 20260-53-1 ]
[ 114346-31-5 ]
[ 136030-33-6 ]
[ 82379-38-2 ]
p-MBHA resin [ No CAS ]
C₃₈H₃₆N₅O₉Pol [ No CAS ]

Reference： [1]Biopolymers,2013,vol. 100,p. 662 - 674

35
[ 1013-24-7 ]
[ 4509-90-4 ]
[ 136030-33-6 ]
(S)-2-(5-(4-(2-(methylthio)phenyl)piperazin-1-yl)pentanoyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide [ No CAS ]