[ CAS No. 133081-25-1 ] {[proInfo.proName]}

Name: 133081-25-1|6-(2-(tert-Butoxycarbonyl)hydrazinyl)nicotinic acid|95%
Brand: Ambeed
SKU: A257341
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Quality Control of [ 133081-25-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 133081-25-1 ]

Product Details of [ 133081-25-1 ]

CAS No. :	133081-25-1	MDL No. :	MFCD03788696
Formula :	C₁₁H₁₅N₃O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DBNGJNCAXKNLLQ-UHFFFAOYSA-N
M.W :	253.25	Pubchem ID :	11311327
Synonyms :

Calculated chemistry of [ 133081-25-1 ]

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.36
Num. rotatable bonds :	6
Num. H-bond acceptors :	5.0
Num. H-bond donors :	3.0
Molar Refractivity :	64.24
TPSA :	100.55 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.72 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.73
Log Po/w (XLOGP3) :	1.59
Log Po/w (WLOGP) :	1.44
Log Po/w (MLOGP) :	-0.21
Log Po/w (SILICOS-IT) :	-0.14
Consensus Log Po/w :	0.88

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-2.26
Solubility :	1.38 mg/ml ; 0.00546 mol/l
Class :	Soluble
Log S (Ali) :	-3.31
Solubility :	0.123 mg/ml ; 0.000487 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.41
Solubility :	0.992 mg/ml ; 0.00392 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.59

Safety of [ 133081-25-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 133081-25-1 ]

* 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.

Upstream synthesis route of [ 133081-25-1 ]
Downstream synthetic route of [ 133081-25-1 ]

[ 133081-25-1 ] Synthesis Path-Upstream 1~7

1
[ 133081-25-1 ]
[ 133081-24-0 ]

Reference： [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 6, p. 1418 - 1422
[2] Journal of Medicinal Chemistry, 2007, vol. 50, # 6, p. 1418 - 1422

2
[ 123-56-8 ]
[ 133081-25-1 ]
[ 133081-26-2 ]

Yield	Reaction Conditions	Operation in experiment
84%	With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 25℃; for 17 h; Inert atmosphere	To a solution of 6-Boc-hydrazinopyridine-3-carboxylicacid 4b (0.57 g, 2.26 mmol) and N-hydrosuccinimide (0.27g, 2.26 mmol) in DMF DCC (0.47 g, 2.26 mmol) was added.The reaction mixture became cloudy after 1h. After 16h, thereaction mixture was concentrated to dryness and the residuewas purified by chromatography on silica gel with ethyl acetateas eluant to give a white solid (0.66 g, 84percent). Mp =174°C. IR (ATR, cm-1) 3321; 2979; 1729; 1594; 1365; 1240;1198; 1068; 974; 641. 1H NMR (DMSO) 9.46 (s, 1H), 9.20(s, 1H), 8.76 (d, 1H, J= 2.1 Hz), 8.11 (d, 1H, J= 8.1 Hz),6.67 (d, 1H, J= 9 Hz), 2.88 (s, 4H), 1.44 (s, 9H). 13C NMR(DMSO) 172.8; 170.5; 160.9; 155.4; 151.8; 110.0; 79.6;28.0; 25.5. MS (ESI+) [M+H]: 351.00. HRMS (ESI+)[M+H]+: 351.1299 observed, 351.1305 calculated forC15H19N4O6.

Reference： [1] Letters in Organic Chemistry, 2014, vol. 11, # 3, p. 208 - 214

3
[ 6066-82-6 ]
[ 133081-25-1 ]
[ 133081-26-2 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 16, p. 4764 - 4767
[2] Journal of Labelled Compounds and Radiopharmaceuticals, 1997, vol. 40, p. 455 - 457
[3] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 12, p. 3440 - 3444
[4] RSC Advances, 2015, vol. 5, # 113, p. 93374 - 93385
[5] Journal of Labelled Compounds and Radiopharmaceuticals, 2017, vol. 60, # 9, p. 431 - 438

4
[ 133081-24-0 ]
[ 24424-99-5 ]
[ 133081-25-1 ]

Yield	Reaction Conditions	Operation in experiment
96%	With triethylamine In N,N-dimethyl-formamide at 25℃; for 17 h; Inert atmosphere	To a solution of 6-hydrazinopyridine-3-carboxylic acid4a (0.346 g, 1.82 mmol) and triethylamine (0.32 mL, 2.36mmol) in DMF di-tert-butyldicarbonate (0.40 g, 1.82 mmol)was added. The mixture became homogenous after 1h. Stirringwas continued over 16h at 25°C then solvent was removedunder reduced pressure. The residue was diluted withethyl acetate/MeOH (4:1) and filtered through silica withethyl acetate as eluant to give 6-Boc-hydrazinopyrridine-3-carboxylic acid 4b as a pale yellow solid (0.44 g, 96percent). IR(ATR, cm-1) 3353; 3227; 2975; 1719; 1593; 1472; 1372;1256; 1014; 867; 794; 520. 1H NMR (DMSO-d6) 12.584(s, 1H); 8.59 (s, 1H); 7.97 (d, 1H, J= 9 Hz); 6.54 (d, 1H, J=9 Hz). 13C NMR (DMSO) 166.6; 155.7; 150.5; 138.5;116.7; 79.3; 28.1; 14.0. MS (ESI-) [M-H]: 252.00. MS (ESI+)[M+H]: 254.07. HRMS (ESI+) [M+H]+: 254.1145 observed,254.1141 calculated for C11H16N3O4.
24%	With triethylamine In N,N-dimethyl-formamide at 65℃; for 15 h;	Synthesis of 6-(2-(tert-butoxycarbonyl)hydrazinyl)nicotinic acidTo a suspension of 6-hydrazinylnicotinic acid (3 g, 19.6 mmol) in DMF (20 mL) was added TEA (2.97 g, 29.4 mmol) and Boc2O (4.7 g, 21.6 mmol). The suspension was heated to 65°C with stirring for 15 hrs. The suspension was poured into water (20 mL) and adjusted pH to 6 with HC1 (1 M) and then purified by reverse phase biotage to give 1.2 g solid (24percent).

Reference： [1] Letters in Organic Chemistry, 2014, vol. 11, # 3, p. 208 - 214
[2] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 16, p. 4764 - 4767
[3] Polish Journal of Chemistry, 2004, vol. 78, # 7, p. 951 - 959
[4] Journal of Labelled Compounds and Radiopharmaceuticals, 2018, vol. 61, # 2, p. 68 - 76
[5] Pharmazie, 2006, vol. 61, # 4, p. 269 - 273
[6] Bioorganic Chemistry, 2011, vol. 39, # 4, p. 138 - 142
[7] Patent: WO2013/67597, 2013, A1, . Location in patent: Page/Page column 91
[8] Journal of Labelled Compounds and Radiopharmaceuticals, 1997, vol. 40, p. 455 - 457
[9] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 12, p. 3440 - 3444
[10] Patent: US5206370, 1993, A,
[11] RSC Advances, 2015, vol. 5, # 113, p. 93374 - 93385
[12] Patent: WO2017/177144, 2017, A1, . Location in patent: Paragraph 33; 39

5
[ 24424-99-5 ]
[ 133081-25-1 ]

Reference： [1] Journal of Medicinal Chemistry, 2002, vol. 45, # 26, p. 5802 - 5805

6
[ 5326-23-8 ]
[ 133081-25-1 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 12, p. 3440 - 3444
[2] Journal of Labelled Compounds and Radiopharmaceuticals, 1997, vol. 40, p. 455 - 457
[3] Bioorganic Chemistry, 2011, vol. 39, # 4, p. 138 - 142
[4] Patent: WO2013/67597, 2013, A1,
[5] Letters in Organic Chemistry, 2014, vol. 11, # 3, p. 208 - 214
[6] RSC Advances, 2015, vol. 5, # 113, p. 93374 - 93385
[7] Journal of Labelled Compounds and Radiopharmaceuticals, 2017, vol. 60, # 9, p. 431 - 438
[8] Patent: WO2017/177144, 2017, A1,

7
[ 133081-24-0 ]
[ 34619-03-9 ]
[ 133081-25-1 ]

Reference： [1] Journal of Labelled Compounds and Radiopharmaceuticals, 2017, vol. 60, # 9, p. 431 - 438

[ 133081-25-1 ] Synthesis Path-Downstream 1~88

1
[ 100-36-7 ]
[ 133081-25-1 ]
[ 485399-97-1 ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,1997,vol. 40,p. 416 - 418
[2]Journal of Medicinal Chemistry,2002,vol. 45,p. 5802 - 5805

2
[ 133081-25-1 ]
Carbonic acid 6-amino-hexyl ester (3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester; compound with trifluoro-acetic acid [ No CAS ]
carbonic acid 6-[6-(N'-tert-butoxycarbonyl-hydrazino)-pyridine-3-carbonyl]-amino}-hexyl ester 17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester [ No CAS ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,1999,vol. 42,p. 23 - 28

3
[ 133081-25-1 ]
9-fluorenylmethyl N-(2-aminoethyl)carbamate hydrochloride [ No CAS ]
resin bound octapeptide Boc-D-Phe-Cys(Acm)-Tyr(t-Bu)-D-Trp(Boc)-Lys(Boc)-Thr(t-Bu)-Cys(Acm)-Thr(resin)-O-allyl [ No CAS ]
C₅₇H₇₅N₁₅O₁₂S₂ [ No CAS ]

Reference： [1]Tetrahedron Letters,2002,vol. 43,p. 5021 - 5024

4
[ 133081-25-1 ]
resin bound octapeptide Fmoc-D-Phe-Cys(Acm)-Tyr(t-Bu)-D-Trp(Boc)-Lys(Boc)-Thr(t-Bu)-Cys(Acm)-Thr(resin)-O-allyl [ No CAS ]
C₅₅H₆₉N₁₃O₁₃S₂ [ No CAS ]

Reference： [1]Tetrahedron Letters,2002,vol. 43,p. 5021 - 5024

5
TGRAKRRMQYNRR [ No CAS ]
[ 133081-25-1 ]
TGRAKRRMQYNRR, conjugate with 6-hydrazinopyridine-3-carboxylic acid [ No CAS ]

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,2005,vol. 48,p. 683 - 691

6
[ 133081-25-1 ]
NH₂CH₂CH₂CH₂CO-Tyr(OtBu)-Pro-(D-Nal)-Pro-NH-(MBHA Rink Amide resin) [ No CAS ]
N-{3-[(S)-2-{(S)-2-[(R)-1-Benzyl-2-((S)-2-carbamoyl-pyrrolidin-1-yl)-2-oxo-ethylcarbamoyl]-pyrrolidin-1-yl}-1-(4-hydroxy-naphthalen-1-ylmethyl)-2-oxo-ethylcarbamoyl]-propyl}-6-hydrazino-nicotinamide [ No CAS ]

Reference： [1]Polish Journal of Chemistry,2004,vol. 78,p. 951 - 959

7
[ 133081-25-1 ]
NH₂CH₂CH₂CH₂CO-Tyr(OtBu)-Pro-(D-Phe)-Pro-NH-(MBHA Rink Amide resin) [ No CAS ]
N-{3-[(S)-2-{(S)-2-[(R)-1-Benzyl-2-((S)-2-carbamoyl-pyrrolidin-1-yl)-2-oxo-ethylcarbamoyl]-pyrrolidin-1-yl}-1-(4-hydroxy-benzyl)-2-oxo-ethylcarbamoyl]-propyl}-6-hydrazino-nicotinamide [ No CAS ]

Reference： [1]Polish Journal of Chemistry,2004,vol. 78,p. 951 - 959

8
[ 133081-25-1 ]
NH₂CH₂CH₂CH₂CO-Tyr(OtBu)-Pro-Phe-Phe-NH-(MBHA Rink Amide resin) [ No CAS ]
N-{3-[(S)-2-{(S)-2-[(S)-1-((S)-1-Carbamoyl-2-phenyl-ethylcarbamoyl)-2-phenyl-ethylcarbamoyl]-pyrrolidin-1-yl}-1-(4-hydroxy-benzyl)-2-oxo-ethylcarbamoyl]-propyl}-6-hydrazino-nicotinamide [ No CAS ]

Reference： [1]Polish Journal of Chemistry,2004,vol. 78,p. 951 - 959

9
[ 133081-25-1 ]
NH₂CH₂CH₂CH₂CO-Tyr(OtBu)-Pro-Phe-Pro-NH-(MBHA Rink Amide resin) [ No CAS ]
N-{3-[(S)-2-{(S)-2-[(S)-1-Benzyl-2-((S)-2-carbamoyl-pyrrolidin-1-yl)-2-oxo-ethylcarbamoyl]-pyrrolidin-1-yl}-1-(4-hydroxy-benzyl)-2-oxo-ethylcarbamoyl]-propyl}-6-hydrazino-nicotinamide [ No CAS ]

Reference： [1]Polish Journal of Chemistry,2004,vol. 78,p. 951 - 959

10
N-(5-aminopentyl)maleimide trifluoroacetic acid salt [ No CAS ]
[ 133081-25-1 ]
[ 873655-99-3 ]

Reference： [1]Dalton Transactions,2005,p. 3886 - 3897

11
[ 57165-75-0 ]
[ 133081-25-1 ]
[ 890436-46-1 ]

Reference： [1]Pharmazie,2006,vol. 61,p. 269 - 273
[2]Bioorganic Chemistry,2019,vol. 91

12
[ 133081-25-1 ]
[ 249290-17-3 ]
[ 890436-53-0 ]

Reference： [1]Pharmazie,2006,vol. 61,p. 269 - 273
[2]Bioorganic Chemistry,2019,vol. 91

13
[ 133081-25-1 ]
[ 249290-19-5 ]
[ 890436-48-3 ]

Reference： [1]Pharmazie,2006,vol. 61,p. 269 - 273
[2]Bioorganic Chemistry,2019,vol. 91

14
[ 133081-25-1 ]
[ 844874-03-9 ]
[ 890436-47-2 ]

Reference： [1]Pharmazie,2006,vol. 61,p. 269 - 273
[2]Bioorganic Chemistry,2019,vol. 91

15
6-hydrazinonicotinic acid hydrochloride [ No CAS ]
[ 24424-99-5 ]
[ 133081-25-1 ]

Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 5802 - 5805

16
[ 133081-25-1 ]
[ 133081-24-0 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 1418 - 1422
[2]Journal of Medicinal Chemistry,2007,vol. 50,p. 1418 - 1422

17
[ 76-05-1 ]
[ 133081-25-1 ]
6-(2-(2,2,2-trifluoroacetyl)hydrazinyl)nicotinic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 1418 - 1422

18
[ 5326-23-8 ]
[ 133081-25-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 3440 - 3444
[2]Journal of labelled compounds and radiopharmaceuticals,1997,vol. 40,p. 455 - 457
[3]Bioorganic Chemistry,2011,vol. 39,p. 138 - 142
[4]Patent: WO2013/67597,2013,A1
[5]Letters in Organic Chemistry,2014,vol. 11,p. 208 - 214
[6]RSC Advances,2015,vol. 5,p. 93374 - 93385
[7]Journal of labelled compounds and radiopharmaceuticals,2017,vol. 60,p. 431 - 438
[8]Patent: WO2017/177144,2017,A1
[9]Bioorganic Chemistry,2019,vol. 91

19
[ 133081-25-1 ]
[ 945034-48-0 ]