227279-10-9

Basic information

• Product Name: 5-Aminomethyl-2-cyanothiophene
• Synonyms: 5-Aminomethyl-2-cyanothiophene;5-(aminomethyl)-2-Thiophenecarbonitrile
• CAS NO: 227279-10-9
• Molecular Formula: C₆H₆N₂S
• Molecular Weight: 138.19024
• Mol File: 227279-10-9.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 5-Aminomethyl-2-cyanothiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Aminomethyl-2-cyanothiophene(227279-10-9)
• EPA Substance Registry System: 5-Aminomethyl-2-cyanothiophene(227279-10-9)

Safety Data

• Hazardous Substances Data: 227279-10-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-Aminomethyl-2-cyanothiophene is used as a building block in the synthesis of various drugs and biologically active compounds, contributing to the development of new therapeutic agents.
Used in Materials Science:
5-Aminomethyl-2-cyanothiophene is utilized in the research and development of novel materials, leveraging its unique chemical properties to create innovative materials with specific applications.
Used in Organic Electronic Devices:
5-Aminomethyl-2-cyanothiophene is employed in the development of organic electronic devices, such as organic light-emitting diodes (OLEDs) and organic photovoltaics, due to its electronic properties and potential for integration into device structures.
Used as a Reagent in Organic Chemistry:
5-Aminomethyl-2-cyanothiophene is used as a reagent in various organic chemical reactions, facilitating the synthesis of complex organic molecules and contributing to the advancement of organic chemistry.

Upstream product

• 554-14-3 2-Methylthiophene 
• 172349-09-6 5-(hydroxymethyl)thiophene-2-carbonitrile 
• 134135-41-4 5-(bromomethyl)thiophene-2-carbonitrile 
• 72835-25-7 2-cyano-5-methylthiophene 
• 765-58-2 2-bromo-5-methyl thiophene 
• 201799-21-5 5-(N,N-Boc₂-aminomethyl)thiophene-2-carbonitrile 
• 368426-18-0 2-cyano-5-(azidomethyl)thiophene 
• 79387-71-6 (5-bromothien-2-yl)methanol 
• 4701-17-1 5-bromo-2-thiophencarboxaldehyde 

Downstream Products

• 203792-55-6 C₃₁H₄₄N₄O₆S 
• 280781-54-6 N-(tert-butoxycarbonyl)methyl-D-diphenylalanyl-L-prolyl-[(5-cyano-2-thienyl)methyl]amide 
• 280781-37-5 (S)-1-((R)-2-Methanesulfonylamino-3,3-diphenyl-propionyl)-pyrrolidine-2-carboxylic acid (5-cyano-thiophen-2-ylmethyl)-amide 
• 785764-66-1 D-diphenylalanyl-L-prolyl-[(5-cyano-2-thienyl)methyl]amide 
• 280781-39-7 N-Boc-D-diphenylalanyl-L-prolyl-[(5-cyano-2-thienyl)methyl]amide 

Relevant articles and documents

Efficacious and orally bioavailable thrombin inhibitors based on a 2,5-thienylamidine at the P1 position: Discovery of N-carboxymethyl-D-diphenylalanyl-L-prolyl[(5-amidino-2- thienyl)methyllamide

Thrombin, a crucial enzyme in the blood coagulation, has been a target for antithrombotic therapy. Orally active thrombin inhibitors would provide effective and safe prophylaxis for venous and arterial thrombosis. We conducted optimization of a highly efficacious benzamidine-based thrombin inhibitor LB30812 (3, Ki = 3 pM) to improve oral bioavailability. Of a variety of arylamidines investigated at the P1 position, 2,5-thienylamidine effectively replaced the benzamidine without compromising the thrombin inhibitory potency and oral absorption. The sulfamide and sulfonamide derivatization at the N-terminal position in general afforded highly potent thrombin inhibitors but with moderate oral absorption, while the well-absorbable N-carbamate derivatives exhibited limited metabolic stability in S9 fractions. The present work culminated in the discovery of the N-carboxymethyl- and 2,5-thienylamidine-containing compound 22 that exhibits the most favorable profiles of anticoagulant and antithrombotic activities as well as oral bioavilability (Ki = 15 pM; F = 43%, 42%, and 15% in rats, dogs, and monkeys, respectively). This compound on a gravimetric basis was shown to be more effective than a low molecular weight heparin, enoxaparin, in the venous thrombosis models of rat and rabbit. Compound 22 (LB30870) was therefore selected for further preclinical and clinical development.

Thrombin inhibitors having a lactam at P3

The present invention provides compounds having a lactam ring at P3 and at P1 have a six-membered heterocyclic ring having two ring nitrogen ring atoms and the remainder of the ring atoms carbon atoms. These compounds have biological activity as active and potent inhibitors of thrombin. Their pharmaceutically acceptable salts, pharmaceutical compositions thereof and methods of using these compounds and pharmaceutical compositions comprising these compounds as therapeutic agents for treatment of disease states in mammals which are characterized by abnormal thrombosis are also described.

Non-covalent inhibitors of urokinase and blood vessel formation

Novel compounds having activity as non-covalent inhibitors of urokinase and having activity in reducing or inhibiting blood vessel formation are provided. These compounds have P1 a group having an amidino or guanidino moiety or derivative thereof. These compounds are useful in vitro for monitoring plasminogen activator levels and in vivo in treatment of conditions which are ameliorated by inhibition of or decreased activity of urokinase and in treating pathologic conditions wherein blood vessel formation is related to a pathologic condition.

Novel, potent non-covalent thrombin inhibitors incorporating P3-lactam scaffolds

Evolution of P1-argininal inhibitor prototypes led to a series of non-covalent P3-7-membered lactam inhibitors 1a-w, featuring novel peptidomimetic units that probe each of the S1, S2, and S3 specificity pockets of thrombin. Rigid P1-arginine surrogates possessing a wide range of basicity (calcd pKa's～neutral-14) were surveyed. The design, synthesis, and biological activity of these targets are presented.

Noncovalent tripeptidic thrombin inhibitors incorporating amidrazone, amine and amidine functions at P1

A series of noncovalent tripeptidic thrombin inhibitors incorporating amidrazone, amine and amidine functions at P1 was investigated. While the amidrazone and the amine series displayed limited oral absorption, the amidine series demonstrated generally good oral absorption and strong antithrombotic activity; the single-digit picomolar Ki achieved from this series is among the best yet reported. The present work highlights the benzamidine compound 11f (LB30812) that exhibits excellent overall profiles of potency, oral absorption and antithrombotic efficacy.

Non-covalent inhibitors of urokinase and blood vessel formation

Novel compounds having activity as non-covalent inhibitors of urokinase and having activity in reducing or inhibiting blood vessel formation are provided. These compounds have Pi a group having an amidino or guanidino moiety or derivative thereof. These compounds are useful in vitro for monitoring plasminogen activator levels and in vivo in treatment of conditions which are ameliorated by inhibition of or decreased activity of urokinase and in treating pathologic conditions wherein blood vessel formation is related to a pathologic condition.