56657-76-2

Basic information

• Product Name: CYANOACETIC ACID-OSU
• Synonyms: CYANOACETIC ACID-OSU;Succinimidyl Cyanoacetate;Acetic acid, 2-cyano-, 2,5-dioxo-1-pyrrolidinyl ester;2,5-Dioxopyrrolidin-1-yl 2-cyanoacetate;2,5-Dioxopyrrolidin-1-yl cyanoacetate;2,5-Pyrrolidinedione, 1-[(cyanoacetyl)oxy]-;N-(Cyanoacetoxy)succinimide;Cyanoacetic acid 2,5-dioxopyrrolidin-1-yl ester
• CAS NO: 56657-76-2
• Molecular Formula: C₇H₆N₂O₄
• Molecular Weight: 182.13
• EINECS: 1592732-453-0
• Mol File: 56657-76-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 336.064°C at 760 mmHg
• Flash Point: 157.046°C
• Appearance: /
• Density: 1.468g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.53
• Storage Temp.: 2-8°C
• PKA: 0.74±0.10(Predicted)
• CAS DataBase Reference: CYANOACETIC ACID-OSU(CAS DataBase Reference)
• NIST Chemistry Reference: CYANOACETIC ACID-OSU(56657-76-2)
• EPA Substance Registry System: CYANOACETIC ACID-OSU(56657-76-2)

Safety Data

• Hazardous Substances Data: 56657-76-2(Hazardous Substances Data)

Usage

Description

CYANOACETIC ACID-OSU, also known as Cyanoacetic Acid N-Hydroxysuccinimide Ester, is a chemical compound commonly utilized as a pharmaceutical intermediate. It is characterized by its ability to form substituted pyrrolopyrimidinamines, which are selective Janus kinase inhibitors.

Uses

Used in Pharmaceutical Industry:
CYANOACETIC ACID-OSU is used as a pharmaceutical intermediate for the synthesis of substituted pyrrolopyrimidinamines. These compounds serve as selective Janus kinase inhibitors, which are crucial in the treatment of autoimmune diseases and organ transplant rejection. The inhibition of Janus kinases helps regulate the immune response, reducing inflammation and preventing the body from attacking its own tissues or the transplanted organ.

InChI:InChI=1/C7H6N2O4/c8-4-3-7(12)13-9-5(10)1-2-6(9)11/h1-3H2

Upstream product

• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 372-09-8 cyanoacetic acid 

Downstream Products

• 870640-28-1 N-[2-benzyloxy-3-(2-cyanoacetylamino)propyl]-2-cyanoacetamide 
• 870640-38-3 N-{2-(2-cyanoacetylamino)-1-[1-(2-cyanoacetylamino)methyl]ethyl}benzamide 
• 1259404-17-5 tasocitinib 
• 540737-29-9 Tofacitinib citrate 
• 1198764-48-5 2-Cyano-N-{5-[3-(6-dimethylamino-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl)-2-hydroxymethyl-phenyl]-1-methyl-2-oxo-1,2-dihydro-pyridin-3-yl}-acetamide 
• 540737-29-9 3-((3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)-3-oxopropanenitrile monocitrate 
• 1313279-94-5 (R)-benzyl 4-(6-(1-(2-cyanoacetyl)piperidin-3-ylamino)-2-(6-fluoroimidazo[1,2-a]pyridin-3-yl)pyrimidin-4-yl)piperazine-1-carboxylate 

Relevant articles and documents

PYRAZOLE DERIVATIVES AS JAK INHIBITORS

New pyrazole derivatives having the chemical structure of formula (I) are disclosed; as well as process for their preparation, pharmaceutical compositions comprising them and their use in therapy as inhibitors of Janus Kinases (JAK).

Small molecule inhibitors of dynamin I GTPase activity: Development of dimeric tyrphostins

Dynamin I is a GTPase enzyme required for endocytosis and is an excellent target for the design of potential endocytosis inhibitors. Screening of a library of tyrphostins, in our laboratory, against the GTPase activity of dynamin I gave rise to a ìèpotent lead, 2-cyano-3-(3,4- dihydroxyphenyl)thioacrylamide (1, IC50 70 μM). Our initial investigations suggested that only the dimeric form of 1 displayed dynamin I GTPase inhibitory activity. Subsequent synthetic iterations were based on dimeric analogues and afforded a number of small molecules, low μM potent, inhibitors of dynamin I GTPase, in particular, symmetrical analogues with a minimum of two free phenolic -OHs: catechol-acrylamide (9) (IC50 = 5.1 ± 0.6 μM), its 3,4,5-trihydroxy congener (10) (IC50 = 1.7 ± 0.2 μM), and the corresponding 3-methyl ether (11) (IC 50 = 9 ± 3 μM). Increasing the length of the central alkyl spacer from ethyl to propyl (22-24) afforded essentially identical activity with IC50's of 1.7 ± 0.2, 1.7 ± 0.2, and 5 ± 1 μM, respectively. No decrease in activity was noted until the introduction of a hexyl spacer. Our studies highlight the requirement for two free amido NHs with neither the mono-N-methyl (86) nor the bis-N-methyl (87) analogues inhibiting dynamin I GTPase. A similar effect was noted for the removal of the nitrile moieties. However, modest potency was observed with the corresponding ester analogues of 9-11: ethyl ester (90), propyl ester (91), and butyl ester (92), with IC50's of 42 ± 3, 38 ± 2, and 61 ± 2 μM, respectively. Our studies reveal the most potent and promising dynamin I GTPase inhibitor in this series as (22), which is also known as BisT.

Rifamycins as inhibitors of retroviral reverse transcriptase from M-MuLV, RAV-2, and HIV-1

29 Rifamycins were tested for inhibition of Reverse Transcriptase (RT) as potential anti HIV drugs. Two purified commercial enzymes from M-MuLV and RAV-2 were used. Anti-RT activity was also measured on a crude lysate of HIV-1. The results show that some derivatives have interesting levels of activity on isolated M-MuLV and RAV-2 RTs, while they are less active on the RT in the crude HIV-1 lysate. The active derivatives include oximes and hydrazones, alkylaminoderivatives, open ansa-chain derivatives and derivatives carrying a modified nucleoside.