59490-98-1

Basic information

• Product Name: N-[2-(aminocarbonyl)phenyl]-2-thiophenecarboxamide
• Synonyms: N-(2-carbamoylphenyl)thiophene-2-carboxamide;N-[2-(aminocarbonyl)phenyl]-2-thiophenecarboxamide;2-Thiophenecarboxamide, N-[2-(aminocarbonyl)phenyl]-
• CAS NO: 59490-98-1
• Molecular Formula: C₁₂H₁₀N₂O₂S
• Molecular Weight: 246.29
• Mol File: 59490-98-1.mol
• Article Data: 3

Chemical Properties

• Melting Point: 280-283 °C(Solv: methanol (67-56-1))
• Boiling Point: 359.8±22.0 °C(Predicted)
• Appearance: /
• Density: 1.395±0.06 g/cm3(Predicted)
• PKA: 12.11±0.70(Predicted)
• CAS DataBase Reference: N-[2-(aminocarbonyl)phenyl]-2-thiophenecarboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-[2-(aminocarbonyl)phenyl]-2-thiophenecarboxamide(59490-98-1)
• EPA Substance Registry System: N-[2-(aminocarbonyl)phenyl]-2-thiophenecarboxamide(59490-98-1)

Safety Data

• Hazardous Substances Data: 59490-98-1(Hazardous Substances Data)

Upstream product

• 527-72-0 2-thiophenylcarboxylic acid 
• 351184-28-6 N-(2-carboxyphenyl)thiophene-2-thiocarboxamide 
• 351184-25-3 2-(2-thienyl)-4H-3,1-benzothiazin-4-one 
• 16024-82-1 methyl 2-isothiocyanatobenzoate 
• 26060-06-0 2-Thiophen-2-yl-4H-3,1-benzoxazin-4-one 
• 5271-67-0 2-Thiophenecarbonyl chloride 
• 28144-70-9 anthranilic acid amide 

Downstream Products

• 1264533-94-9 2-(thiophen-2-yl)-4-(1-tosylpiperidin-4-yl)quinazoline 
• 59455-95-7 4-chloro-2-(thien-2-yl)quinazoline 

Relevant articles and documents

Evaluation of quinazoline analogues as glucocerebrosidase inhibitors with chaperone activity

Gaucher disease is a lysosomal storage disorder (LSD) caused by deficiency in the enzyme glucocerebrosidase (GC). Small molecule chaperones of protein folding and translocation have been proposed as a promising therapeutic approach to this LSD. Most small molecule chaperones described in the literature contain an iminosugar scaffold. Here we present the discovery and evaluation of a new series of GC inhibitors with a quinazoline core. We demonstrate that this series can improve the translocation of GC to the lysosome in patient-derived cells. To optimize this chemical series, systematic synthetic modifications were performed and the SAR was evaluated and compared using three different readouts of compound activity: enzymatic inhibition, enzyme thermostabilization, and lysosomal translocation of GC.

Discovery of potent cyclic GMP phosphodiesterase inhibitors. 2-Pyridyl- and 2-imidazolylquinazolines possessing cyclic GMP phosphodiesterase and thromboxane synthesis inhibitory activities

Moderate cyclic GMP phosphodiesterase (cGMP-PDE, PDE V) inhibitor 2- phenyl-4-anilino-quinazoline (1) was identified utilizing MultiCASE assisted drug design (MCADD) technology. Modification of compound 1 was conducted at the 2-, 4-, and 6-positions of the quinazoline ring for enhancement of cGMP- PDE inhibitory activity. The 6-substituted 2-(imidazol-1-yl)-quinazolines are 1000 times more potent in in vitro PDE V enzyme assay than the well-known inhibitor zaprinast. The 6-substituted derivatives of 2-(3- pyridyl)quinazoline 84 and 2-(imidazol-1-yl)quinazoline 86 exhibited more than 1000-fold selectivity for PDE V over the other four PDE isozymes. In addition, cGMP-PDE inhibitors 64, 65, and 73 were found to have an additional property of thromboxane synthesis inhibitory activity.