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

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

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

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.

Identification of a new class of potent Cdc7 inhibitors designed by putative pharmacophore model: Synthesis and biological evaluation of 2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-ones

Cell division cycle 7 (Cdc7) is a serine/threonine kinase that plays important roles in the regulation of DNA replication process. A genetic study indicates that Cdc7 inhibition can induce selective tumor-cell death in a p53-dependent manner, suggesting that Cdc7 is an attractive target for the treatment of cancers. In order to identify a new class of potent Cdc7 inhibitors, we generated a putative pharmacophore model based on in silico docking analysis of a known inhibitor with Cdc7 homology model. The pharmacophore model provided a minimum structural motif of Cdc7 inhibitor, by which preliminary medicinal chemistry efforts identified a dihydrothieno[3,2-d]-pyrimidin-4(1H)-one scaffold having a heteroaromatic hinge-binding moiety. The structure-activity relationship (SAR) studies resulted in the discovery of new, potent, and selective Cdc7 inhibitors 14a, c, e. Furthermore, the high selectivity of 14c, e for Cdc7 over Rho-associated protein kinase 1 (ROCK1) is discussed by utilizing a docking study with Cdc7 and ROCK2 crystal structures.

HETEROCYCLIC COMPOUND

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

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

THIOPHENE-CARBOXAMIDE DERIVATIVES AND THEIR USE AS INHIBITORS OF THE ENZIME IKK-2

The invention relates to thiophene carboxamides of formula (I), wherein A, R1, R2, R3, R4, R5 and X are as defined in the specification, processes and intermediates used in their preparation, pharmaceutical compositions containing them and their use in therapy.

THIOPHENE CARBOXAMIDES AS INHIBITORS OF THE ENZYME IKK-2

The invention relates to thiophene carboxamides of formula (I) wherein Ar, R1, R2, R3, R4, R5, m and n are as defined in the specification, processes and intermediates used in their preparation, pharmaceutical compositions containing them and their use in therapy.