784124-87-4

Basic information

• Product Name: 2-Thiophenecarboxamide,4-amino-(9CI)
• Synonyms: 2-Thiophenecarboxamide,4-amino-(9CI);4-aminothiophene-2-carboxamide
• CAS NO: 784124-87-4
• Molecular Formula: C₅H₆N₂OS
• Molecular Weight: 142.17894
• Product Categories: AMIDE
• Mol File: 784124-87-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Thiophenecarboxamide,4-amino-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Thiophenecarboxamide,4-amino-(9CI)(784124-87-4)
• EPA Substance Registry System: 2-Thiophenecarboxamide,4-amino-(9CI)(784124-87-4)

Safety Data

• Hazardous Substances Data: 784124-87-4(Hazardous Substances Data)

Upstream product

• 36050-08-5 4-nitrothiophene-2-carboxamide 

Downstream Products

• 224449-27-8 4-(phenyloxycarbonylamino)thiophene-2-carboxamide 

Relevant articles and documents

Pyrrole inhibitors of S-nitrosoglutathione reductase as therapeutic agents

The present invention is directed to inhibitors of S-nitrosoglutathione reductase (GSNOR), pharmaceutical compositions comprising such GSNOR inhibitors, and methods of making and using the same.

Synthesis of thiophenecarboxamides, thieno[3,4-c]pyridin-4(5H)-ones and thieno[3,4-d]pyrimidin-4(3H)-ones and preliminary evaluation as inhibitors of poly(ADP-ribose)polymerase (PARP)

Inhibitors of poly(ADP-ribose)polymerase (PARP) inhibit repair of damaged DNA and thus potentiate radiotherapy and chemotherapy of cancer. Treatment of 3-cyanothiophene with potassium nitrate and concentrated sulphuric acid gave 5-nitrothiophene-3-carboxamide. 4-Nitrothiophene-2-carboxamide and 5-nitrothiophene-2-carboxamide were formed similarly from 2-cyanothiophene. Reduction with tin(II) chloride gave the corresponding aminothiophenecarboxamide salts which were isolated via their N-Cbz derivatives. Lithiation of 3,4-dibromothiophene at -116°C and quenching with alkyl chloroformates gave 4-bromothiophene-3-carboxylates, which were hydrolysed to 4-bromothiophene-3-carboxylic acid. Hurtley reactions with the enolates of pentane-2,4-dione and of 1-phenylbutane-1,3-dione, followed by acyl cleavage, led to 4-(2-oxopropyl)thiophene-3-carboxylic acid and 4-phenacylthiophene-3-carboxylic acid, respectively. Condensation with ammonia in acetic acid gave 6-methyl- and 6-phenyl-thieno[3,4-c]pyridin-4-ones, which were selectively nitrated at the 1- and 7-positions or were dinitrated. Ethyl 4-acetamido- and 4-benzamido-thiophene-3-carboxylates were cyclised to 2-methyl- and 2-phenyl-thieno[3,4-d][1,3]oxazin-4-ones, respectively. Ring-opening with ammonia and recyclisation led to 2-substituted thieno[3,4-d]pyrimidin-4-ones. The aminothiophenecarboxamides are analogues of 3-aminobenzamide, a selective inhibitor of poly(ADP-ribose)polymerase (PARP); the thienopyridinones and the thienopyrimidinones are analogues of isoquinolin-1-ones and quinazolin-4-ones, respectively, which inhibit this enzyme. In preliminary assays, several thienopyridinones and thienopyrimidinones showed potent inhibitory activity against PARP. Copyright (C) 1999 Published by Elsevier Science Ltd.