494833-79-3

Basic information

• Product Name: 2-Thiophenecarboxamide, 3-amino-5-bromo-
• CAS NO: 494833-79-3
• Molecular Formula: C5H5BrN2OS
• Molecular Weight: 221.077
• Mol File: 494833-79-3.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 2-Thiophenecarboxamide, 3-amino-5-bromo-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Thiophenecarboxamide, 3-amino-5-bromo-(494833-79-3)
• EPA Substance Registry System: 2-Thiophenecarboxamide, 3-amino-5-bromo-(494833-79-3)

Safety Data

• Hazardous Substances Data: 494833-79-3(Hazardous Substances Data)

Upstream product

• 494833-78-2 tert-butyl (5-bromo-2-carbamoylthiophen-3-yl)carbamate 
• 1244027-57-3 3-amino-5-bromothiophene-2-carboxylic acid 
• 107818-55-3 3-amino-5-bromo-thiophene-2-carboxylic acid methyl ester 
• 22288-78-4 Methyl 3-aminothiophene-2-carboxylate 
• 852330-31-5 5-bromo-3-(2,2,2-trifluoracetamido)thiophene-2-carboxylic acid methyl ester 
• 79128-68-0 methyl 3-(2,2,2-trifluoroacetamido)thiophene-2-carboxylate 
• 946604-99-5 methyl 5-bromo-3-((tert-butoxycarbonyl)amino)thiophene-2-carboxylate 
• 494833-77-1 5-bromo-3-((tert-butoxycarbonyl)amino)thiophene-2-carboxylic acid 

Downstream Products

• 1330781-03-7 2-(2-chlorophenyl)-6-(5-methyl-1H-pyrazol-4-yl)thieno[3,2-d]pyrimidin-4(3H)-one 
• 1330783-38-4 5-bromo-3-{[phenyl(pyrrolidin-1-yl)acetyl]amino}thiophene-2-carboxamide 
• 1330781-99-1 6-(5-methyl-1H-pyrazol-4-yl)-2-(2-phenyl-1-pyrrolidin-1-ylethyl)thieno[3,2-d]pyrimidin-4(3H)-one 
• 1330784-34-3 (9H-fluoren-9-yl)methyl (1-((5-bromo-2-carbamoylthiophen-3-yl)amino)-2-methyl-1-oxopropan-2-yl)carbamate 
• 1330783-39-5 6-bromo-2-[phenyl(pyrrolidin-1-yl)methyl]thieno[3,2-d]pyrimidin-4(3H)-one 
• 1330781-90-2 6-(5-methyl-1H-pyrazol-4-yl)-2-{1-[4-(methylsulfonyl)phenyl]pyrrolidin-2-yl}thieno[3,2-d]pyrimidin-4(3H)-one 
• 1330783-56-6 6-bromo-2-{1-[4-(methylsulfonyl)phenyl]pyrrolidin-2-yl}thieno[3,2-d]pyrimidin-4(3H)-one 
• 1330783-91-9 benzyl 1-{6-[1-(tert-butoxycarbonyl)-3-methyl-1H-pyrazol-4-yl]-4-oxo-3,4-dihydrothieno[3,2-d]pyrimidin-2-yl}-7-azabicyclo[2.2.1]heptane-7-carboxylate 
• 1330783-90-8 benzyl 1-(6-bromo-4-oxo-3,4-dihydrothieno[3,2-d]pyrimidin-2-yl)-7-azabicyclo[2.2.1]heptane-7-carboxylate 
• 1330783-58-8 N-(5-bromo-2-carbamoylthiophen-3-yl)-1-[4-(methylsulfonyl)phenyl]prolinamide 
• 1330782-91-6 6-bromo-2-phenylthieno[3,2-d]pyrimidin-4(3H)-one 

Relevant articles and documents

SUBSTITUTED [5,6]CYCLIC-4(3H)-PYRIMIDINONES AS ANTICANCER AGENTS

The present invention relates to novel substituted [5,6]cyclic-4(3H)-pyrimidinone compounds of formula (I) and their preparation methods. (I) In particular, the present invention relates to novel substituted [5,6]cyclic-4(3H)- pyrimidinone compounds useful as inhibitors of protein kinases, specifically CDC7 (cell division cycle 7) inhibitors.

2-Aminomethylthieno[3,2-d]pyrimidin-4(3H)-ones bearing 3-methylpyrazole hinge binding moiety: Highly potent, selective, and time-dependent inhibitors of Cdc7 kinase

In order to increase the success rate for developing new Cdc7 inhibitors for cancer therapy, we explored a new chemotype which can comply with the previously-constructed pharmacophore model. Substitution of a pyridine ring of a serendipitously-identified Cdc7 inhibitor 2b with a 3-methylpyrazole resulted in a 4-fold increase in potency and acceptable kinase selectivity, leading to the identification of thieno[3,2-d]pyrimidin-4(3H)-one as an alternative scaffold. Structure-activity relationship (SAR) study revealed that incorporation of a substituted aminomethyl group into the 2-position improved kinase selectivity. Indeed, a pyrrolidinylmethyl derivative 10c was a potent Cdc7 inhibitor (IC50?=?0.70?nM) with high selectivity (Cdk2/Cdc7?≥?14,000, ROCK1/Cdc7?=?200). It should be noted that 10c exhibited significant time-dependent Cdc7 inhibition with slow dissociation kinetics, cellular pharmacodynamic (PD) effects, and COLO205 growth inhibition. Additionally, molecular basis of high kinase selectivity of 10c is discussed by using the protein structures of Cdc7 and Cdk2.

THIENOPYRIMIDINE AS CDC7 KINASE INHIBITORS

The present invention relates to a compound represented by the formula (I): wherein each symbol is as defined in the specification, or a salt thereof, or a prodrug thereof, which is useful for the prophylaxis or treatment of cancer