[ CAS No. 38136-70-8 ] {[proInfo.proName]}

Name: 38136-70-8|(3S,8aS)-3-((1H-Indol-3-yl)methyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione|98%
Brand: Ambeed
SKU: A313042
Price: 21.0 USD
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Quality Control of [ 38136-70-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 38136-70-8 ]

SDS Specification

Alternatived Products of [ 38136-70-8 ]

Product Details of [ 38136-70-8 ]

CAS No. :	38136-70-8	MDL No. :	MFCD29917326
Formula :	C₁₆H₁₇N₃O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RYFZBPVMVYTEKZ-KBPBESRZSA-N
M.W :	283.33	Pubchem ID :	181567
Synonyms :	Cyclo(L-Pro-L-Trp);Cyclo-L-tryptophyl-L-proline;cyclo-(L-Trp-L-Pro)

Calculated chemistry of [ 38136-70-8 ]

Physicochemical Properties

Num. heavy atoms :	21
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.38
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	86.61
TPSA :	65.2 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.96 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.87
Log Po/w (XLOGP3) :	1.51
Log Po/w (WLOGP) :	0.44
Log Po/w (MLOGP) :	0.97
Log Po/w (SILICOS-IT) :	2.14
Consensus Log Po/w :	1.39

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.73
Solubility :	0.524 mg/ml ; 0.00185 mol/l
Class :	Soluble
Log S (Ali) :	-2.49
Solubility :	0.922 mg/ml ; 0.00326 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.33
Solubility :	0.0133 mg/ml ; 0.000047 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.85

Safety of [ 38136-70-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 38136-70-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 38136-70-8 ]

[ 38136-70-8 ] Synthesis Path-Downstream 1~88

1
[ 79982-38-0 ]
[ 38136-70-8 ]

Reference： [1]Tetrahedron Letters,1981,vol. 22,p. 2565 - 2568

2
[ 79982-39-1 ]
[ 38136-70-8 ]

Reference： [1]Tetrahedron Letters,1981,vol. 22,p. 2565 - 2568

3
L-Tryptophyl-L-proline Methyl Ester [ No CAS ]
[ 38136-70-8 ]

Reference： [1]Tetrahedron,1993,vol. 49,p. 3165 - 3184

4
[ 38136-70-8 ]
[ 108-12-3 ]
[ 123251-58-1 ]

Reference： [1]Chemical and pharmaceutical bulletin,1989,vol. 37,p. 23 - 32

5
[ 38136-70-8 ]
[ 79950-62-2 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1985,vol. 33,p. 4783 - 4791
[2]Tetrahedron Letters,1981,vol. 22,p. 2565 - 2568
[3]Tetrahedron Letters,1981,vol. 22,p. 2565 - 2568

6
[ 38136-70-8 ]
[ 79982-38-0 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1985,vol. 33,p. 4783 - 4791
[2]Tetrahedron Letters,1981,vol. 22,p. 2565 - 2568
[3]Chemical and Pharmaceutical Bulletin,1985,vol. 33,p. 4783 - 4791

7
[ 38136-70-8 ]
[ 79982-38-0 ]
[ 79982-39-1 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1985,vol. 33,p. 4783 - 4791
[2]Tetrahedron Letters,1981,vol. 22,p. 2565 - 2568

Yield	Reaction Conditions	Operation in experiment
	In water; at 130℃; for 4h;Autoclave;	General procedure: L- or D-Amino acid methyl ester hydrochloride (0.5 g, 3.6 mmol) was dissolved in 10 mL of dimethylformamide (DMF). Then, diisopropylethylamine (DIEA; 0.78 g, 6.0 mmol), various L- or D-N-Boc-amino acids (3.0 mmol) and O-(benzotriazol-1-yl)-N,N,N,N-tetramethyluronium hexafluorophosphate (HBTU; 1.37 g, 3.6 mmol) were added. After reaction at room temperature for 12 hours while stirring, DMF was removed from the reaction mixture under reduced pressure. The remaining mixture was diluted with ethyl acetate and washed with sodium bicarbonate and brine. The organic layer was concentrated under reduced pressure after removing water with anhydrous sodium sulfate. The concentrate was purified by silica column chromatography (EtOAc/hexane) to obtain a linear N-Boc-dipeptide. The linear N-Boc-dipeptide was added to a round-bottom flask and 20 mL of water added per 1 mmol of the linear N-Boc-dipeptide. Thereafter, the reaction vessel was fixed to a stainless-steel sterilization apparatus equipped with a pressure control valve. The sterilization apparatus was closed and the temperature of the reaction mixture was maintained at 130 °C for 4 hours. After stopping the reaction by lowering temperature, the pressure of the sterilization apparatus was decreased. After removing water under reduced pressure, the remaining concentrate was purified by silica column chromatography (MeOH/MC) to obtain a pure 2,5-diketopiperazine derivative. Nuclear magnetic resonance spectroscopic data of the prepared compounds are given below. They agree well to the data available from literatures.

9
[ 236123-12-9 ]
[ 38136-70-8 ]

Reference： [1]Journal of Chemical Crystallography,1999,vol. 29,p. 435 - 447

10
[ 24424-99-5 ]
[ 38136-70-8 ]
[ 310462-37-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2000,vol. 8,p. 2407 - 2415

11
[ 38136-70-8 ]
[ 870-63-3 ]
2-(3-methyl-but-2-enyl)-3-[1-(3-methyl-but-2-enyl)-1H-indol-3-ylmethyl]-hexahydro-pyrrolo[1,2-a]pyrazine-1,4-dione [ No CAS ]
2-(3-methyl-but-2-enyl)-3-[1-(3-methyl-but-2-enyl)-1H-indol-3-ylmethyl]-hexahydro-pyrrolo[1,2-a]pyrazine-1,4-dione [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2000,vol. 8,p. 2407 - 2415

12
[ 358-72-5 ]
[ 38136-70-8 ]
[ 34610-68-9 ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 9089 - 9098
[2]Journal of the American Chemical Society,2010,vol. 132,p. 12733 - 12740
[3]Organic Letters,2018,vol. 20,p. 7201 - 7205

13
[ 38136-70-8 ]
C₁₆H₁₆FN₃O₂ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2001,vol. 40,p. 4461 - 4463

14
[ 41004-19-7 ]
[ 38136-70-8 ]
[ 179936-52-8 ]
[ 608146-24-3 ]
[ 608146-25-4 ]
[ 336130-47-3 ]

Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 6944 - 6951

15
[ 38136-70-8 ]
[ 870-63-3 ]
[ 76-05-1 ]
[ 336130-50-8 ]

Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 6944 - 6951

16
[ 38136-70-8 ]
[ 870-63-3 ]
[ 179936-52-8 ]
[ 608146-24-3 ]
(5aS,6aS,11aS,13aS)-6a-prenyl-1,2,3,6,6a,11,11a,13a-octahydro-13H-pyrrolo[1'',2''-4',5']pyrazino[2',1'-5,1]pyrrolo[2,3-b]indole-5,13(5aH)-dione [ No CAS ]
[ 336130-47-3 ]

Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 6944 - 6951

17
[ 38136-70-8 ]
[ 870-63-3 ]
[ 608146-24-3 ]
[ 608146-25-4 ]
[ 336130-47-3 ]
(5aS,6aS,11aS,13aS)-6a,11a-diprenyl-1,2,3,6,6a,11,11a,13a-octahydro-13H-pyrrolo[1'',2''-4',5']pyrazino[2',1'-5,1]pyrrolo[2,3-b]indole-5,13(5aH)-dione [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 6944 - 6951

18
[ 608146-30-1 ]
[ 38136-70-8 ]
[ 509078-49-3 ]

Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 6944 - 6951

19
[ 754229-39-5 ]
[ 38136-70-8 ]

Reference： [1]Journal of the Indian Chemical Society,2003,vol. 80,p. 765 - 768

20
[ 38136-70-8 ]
[ 870-63-3 ]
[ 73093-48-8 ]
[ 608146-25-4 ]
[ 336130-47-3 ]

Reference： [1]Organic Letters,2006,vol. 8,p. 4303 - 4306

21
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[ 870-63-3 ]
(8aS)-3-(3'-indolylmethyl)-2-prenyl-1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine-1,4-dione [ No CAS ]
[ 608146-25-4 ]
[ 336130-47-3 ]

Reference： [1]Organic Letters,2006,vol. 8,p. 4303 - 4306

22
[ 13139-14-5 ]
[ 38136-70-8 ]

Reference： [1]Journal of the Indian Chemical Society,2003,vol. 80,p. 765 - 768
[2]Journal of Chemical Crystallography,1999,vol. 29,p. 435 - 447

23
[ 73-22-3 ]
[ 38136-70-8 ]

Reference： [1]Journal of the Indian Chemical Society,2003,vol. 80,p. 765 - 768

24
[ 754229-38-4 ]
[ 38136-70-8 ]

Reference： [1]Journal of the Indian Chemical Society,2003,vol. 80,p. 765 - 768

25
[ 15761-39-4 ]
Boc-MePhe-N(-CH₂-Merrifield resin)-Phe-OMeBoc-Leu-OH [ No CAS ]
[ 38136-70-8 ]

Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 6944 - 6951

26
[ 38136-70-8 ]
[ 179936-52-8 ]

Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 6944 - 6951
[2]Journal of Organic Chemistry,2003,vol. 68,p. 6944 - 6951

27
[ 38136-70-8 ]
(3S,8aS)-3-(2'-(3''-hydroxy-3'',3''-dimethylpropyl)-3'-indolylmethyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 6944 - 6951

28
[ 4299-70-1 ]
[ 38136-70-8 ]

Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 6944 - 6951

29
[ 38136-70-8 ]
3-(1H-indol-3-ylmethyl)-2-(3-methyl-but-2-enyl)-hexahydro-pyrrolo[1,2-a]pyrazine-1,4-dione [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2000,vol. 8,p. 2407 - 2415

30
[ 38136-70-8 ]
[ 310462-38-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2000,vol. 8,p. 2407 - 2415

31
[ 38136-70-8 ]
[ 310462-43-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2000,vol. 8,p. 2407 - 2415

32
[ 7531-52-4 ]
[ 38136-70-8 ]

Reference： [1]Journal of Chemical Crystallography,1999,vol. 29,p. 435 - 447

33
[ 38136-70-8 ]
[ 79982-37-9 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1985,vol. 33,p. 4783 - 4791
[2]Tetrahedron Letters,1981,vol. 22,p. 2565 - 2568

34
[ 38136-70-8 ]
[ 73093-44-4 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1985,vol. 33,p. 4783 - 4791
[2]Chemical and Pharmaceutical Bulletin,1985,vol. 33,p. 4783 - 4791
[3]Chemical and Pharmaceutical Bulletin,1985,vol. 33,p. 4783 - 4791
[4]Tetrahedron Letters,1981,vol. 22,p. 2565 - 2568
[5]Tetrahedron Letters,1981,vol. 22,p. 2565 - 2568

35
[ 38136-70-8 ]
[ 79950-61-1 ]

Reference： [1]Tetrahedron Letters,1981,vol. 22,p. 2565 - 2568
[2]Tetrahedron Letters,1981,vol. 22,p. 2565 - 2568
[3]Tetrahedron Letters,1981,vol. 22,p. 2565 - 2568

36
[ 38136-70-8 ]
[ 79950-60-0 ]

Reference： [1]Tetrahedron Letters,1981,vol. 22,p. 2565 - 2568
[2]Tetrahedron Letters,1981,vol. 22,p. 2565 - 2568
[3]Tetrahedron Letters,1981,vol. 22,p. 2565 - 2568

37
[ 38136-70-8 ]
[ 79950-58-6 ]

Reference： [1]Tetrahedron Letters,1981,vol. 22,p. 2565 - 2568

38
[ 38136-70-8 ]
[ 79950-58-6 ]

Reference： [1]Tetrahedron Letters,1981,vol. 22,p. 2565 - 2568
[2]Tetrahedron Letters,1981,vol. 22,p. 2565 - 2568

39
[ 38136-70-8 ]
[ 79950-57-5 ]

Reference： [1]Tetrahedron Letters,1981,vol. 22,p. 2565 - 2568

40
[ 38136-70-8 ]
[ 79950-57-5 ]

Reference： [1]Tetrahedron Letters,1981,vol. 22,p. 2565 - 2568
[2]Tetrahedron Letters,1981,vol. 22,p. 2565 - 2568

41
[ 38136-70-8 ]
[ 79950-59-7 ]

Reference： [1]Tetrahedron Letters,1981,vol. 22,p. 2565 - 2568
[2]Tetrahedron Letters,1981,vol. 22,p. 2565 - 2568

42
[ 38136-70-8 ]
[ 79950-59-7 ]

Reference： [1]Tetrahedron Letters,1981,vol. 22,p. 2565 - 2568

43
C₁₆H₂₀N₄O₂ [ No CAS ]
[ 38136-70-8 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 25℃; for 15h;	To a solution of N-(t-Boc)-L-Trp-L-ProNH2 (0.60 g, 1.50 mmol) in DCM (10 mL) was added trifluoroacetic acid (5 mL) at 0° C. After 1 h the solution was concentrated under reduced pressure. The crude residue was dissolved in DCM (10 mL) and Et3N (0.5 mL) was added. This solution was stirred at 25° C. for 15 h then washed with saturated NH4Cl (2.x.20 mL), brine (20 mL), dried (Na2SO4), and concentrated under reduced pressure. Flash chromatography on silica gel (EtOAc/MeOH) gave the title compound (Compound 3) (20 mg, 55percent) as a white solid: 1H NMR (CDCl3) d 1.8-2.1 (m, 3H), 2.28-2.4 (m, 1H), 2.97 (dd, 1H, J=10.8, 15.0 Hz), 3.5-3.7 (m, 2H), 3.75 (dd, 1H, J=3.3, 15.0 Hz), 4.07 (bt, 1H, J=7.2 Hz), 4.3-4.45 (m, 1H), 5.79 (bs, 1H), 7.0-7.3 (m, 3H), 7.39 (d, 1H, J=8.1 Hz), 7.59 (d, J=7.8 Hz), 8.47 (bs, 1H); 13C NMR (CDCl3) delta 22.6, 26.8, 28.3, 45.4, 54.5, 59.2, 109.8, 111.6, 118.4, 119.9, 122.7, 123.4, 126.7, 136.6, 165.5, 169.3; GC-MS m/z 283 (M+, 5), 186 (6), 154 (7), 130 (100).

Reference： [1]Patent: US7202279,2007,B1 .Location in patent: Page/Page column 43

44
[ 85416-63-3 ]
[ 38136-70-8 ]

Reference： [1]Tetrahedron Letters,2008,vol. 49,p. 4231 - 4234

45
[ 1186-30-7 ]
[ 38136-70-8 ]
[ 179936-52-8 ]

Reference： [1]Journal of Natural Products,2009,vol. 72,p. 44 - 52

46
[ 38136-70-8 ]
[ 1258943-32-6 ]

Reference： [1]Journal of the American Chemical Society,2010,vol. 132,p. 17849 - 17858

47
[ 15761-39-4 ]
[ 38136-70-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3866 - 3869

48
[ 358-72-5 ]
[ 38136-70-8 ]
[ 179936-52-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3866 - 3869
[2]Organic and Biomolecular Chemistry,2012,vol. 10,p. 9262 - 9270
[3]ChemBioChem,2013,vol. 14,p. 2029 - 2037
[4]Organic Letters,2018,vol. 20,p. 7201 - 7205

49
[ 7524-52-9 ]
[ 38136-70-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3866 - 3869

50
[ 608146-30-1 ]
[ 38136-70-8 ]
[ 38136-70-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3866 - 3869

51
[ 813452-60-7 ]
[ 2133-40-6 ]
[ 38136-70-8 ]

Reference： [1]International Journal of Peptide Research and Therapeutics,2012,vol. 18,p. 7 - 19

52
[ 1343483-76-0 ]
[ 38136-70-8 ]

Reference： [1]International Journal of Peptide Research and Therapeutics,2012,vol. 18,p. 7 - 19

53
[ 55782-87-1 ]
[ 38136-70-8 ]

Reference： [1]International Journal of Peptide Research and Therapeutics,2012,vol. 18,p. 7 - 19
[2]ChemPhysChem,2012,vol. 13,p. 2748 - 2760
[3]Journal of Organic Chemistry,2015,vol. 80,p. 8046 - 8054

54
[ 92178-03-5 ]
[ 38136-70-8 ]

Reference： [1]International Journal of Peptide Research and Therapeutics,2012,vol. 18,p. 7 - 19

55
(3-trifluoroacetamido-4-bromophenyl)(mesityl)iodonium hexafluorophosphate [ No CAS ]
[ 38136-70-8 ]
[ 1429318-79-5 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 5557 - 5560

56
[ 207349-25-5 ]
[ 38136-70-8 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 5557 - 5560

57
[ 204980-52-9 ]
[ 38136-70-8 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 5557 - 5560

58
[ 38136-70-8 ]
[ 1429318-80-8 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 5557 - 5560

59
[ 38136-70-8 ]
[ 1179325-42-8 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 5557 - 5560
[2]Organic Letters,2019,vol. 21,p. 7094 - 7098

60
diphenyl(trifluoromethanesulfonato)-λ³-iodane [ No CAS ]
[ 38136-70-8 ]
[ 1429318-62-6 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 5557 - 5560

61
[ 22342-44-5 ]
[ 38136-70-8 ]
[ 1440540-57-7 ]
[ 1440540-56-6 ]
[ 1440540-58-8 ]
[ 1440540-59-9 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 3062 - 3065

62
[ 929531-71-5 ]
[ 38136-70-8 ]
[ 1440540-61-3 ]
[ 1440540-60-2 ]
[ 1440540-62-4 ]
[ 1440540-63-5 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 3062 - 3065

63
[ 624-31-7 ]
[ 38136-70-8 ]
[ 1454306-26-3 ]