391680-92-5

Basic information

• Product Name: 5,6-DIHYDROXY-2-THIOPHEN-2-YL-PYRIMIDINE-4-CARBOXYLIC ACID METHYL ESTER
• Synonyms: 5,6-DIHYDROXY-2-THIOPHEN-2-YL-PYRIMIDINE-4-CARBOXYLIC ACID METHYL ESTER
• CAS NO: 391680-92-5
• Molecular Formula: C₁₀H₈N₂O₄S
• Molecular Weight: 252.25
• Mol File: 391680-92-5.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5,6-DIHYDROXY-2-THIOPHEN-2-YL-PYRIMIDINE-4-CARBOXYLIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-DIHYDROXY-2-THIOPHEN-2-YL-PYRIMIDINE-4-CARBOXYLIC ACID METHYL ESTER(391680-92-5)
• EPA Substance Registry System: 5,6-DIHYDROXY-2-THIOPHEN-2-YL-PYRIMIDINE-4-CARBOXYLIC ACID METHYL ESTER(391680-92-5)

Safety Data

• Hazardous Substances Data: 391680-92-5(Hazardous Substances Data)

Upstream product

• 1003-31-2 thiophene-2-carbonitrile 
• 53370-51-7 N'-hydroxythiophene-2-carboximidamide 
• 53370-51-7 (Z)-N'-hydroxythiophene-2-carboxamidine 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 878650-00-1 (E)-2-[(Thiophene-2-carboximidoyl)-aminooxy]-but-2-enedioic acid dimethyl ester 
• 878650-00-1 (E)-2-[(Thiophene-2-carboximidoyl)-aminooxy]-but-2-enedioic acid dimethyl ester 

Downstream Products

• 849475-88-3 C-phenyl-N-(5-thiophen-2-yl-[1,3]dioxolo[4,5-d]pyrimidine-7-carbonyl)-methanesulfonamide 
• 766557-52-2 5-benzoyloxy-6-methanesulfonyl-2-thiophen-2-yl-pyrimidine-4-carboxylic acid methyl ester 
• 849544-02-1 5-benzoyloxy-6-methylsulfanyl-2-thiophen-2-yl-pyrimidine-4-carboxylic acid methyl ester 
• 766557-50-0 5-benzoyloxy-6-chloro-2-thiophen-2-yl-pyrimidine-4-carboxylic acid methyl ester 

Relevant articles and documents

From dihydroxypyrimidine carboxylic acids to carboxamide HIV-1 integrase inhibitors: SAR around the amide moiety

4,5-Dihyroxypyrimidine carboxamides, which evolved from a related series of HCV NS5b polymerase inhibitors, have been optimized to provide selective HIV integrase strand transfer inhibitors. Extensive SAR around the benzylamide moiety led to the identification of the p-fluorobenzylamide as optimal in the enzymatic assay.

Dihydroxypyrimidine-4-carboxamides as novel potent and selective HIV integrase inhibitors

Human immunodeficiency virus type-1 (HIV-1) integrase, one of the three constitutive viral enzymes required for replication, is a rational target for chemotherapeutic intervention in the treatment of AIDS that has also recently been confirmed in the clinical setting. We report here on the design and synthesis of N-benzyl-5,6-dihydroxypyrimidine-4-carboxamides as a class of agents which exhibits potent inhibition of the HIV-integrase-catalyzed strand transfer process. In the current study, structural modifications on these molecules were made in order to examine effects on HIV-integrase inhibitory potencies. One of the most interesting compounds for this series is 2-[1-(dimethylamino)-1-methylethyl]-N-(4-fluorobenzyl)-5,6-dihydroxypyrimidine- 4-carboxamide 38, with a CIC95 of 78 nM in the cell-based assay in the presence of serum proteins. The compound has favorable pharmacokinetic properties in preclinical species (rats, dogs, and monkeys) and shows no liabilities in several counterscreening assays, highlighting its potential as a clinically useful antiviral agent.

4,5-Dihydroxypyrimidine carboxamides and N-alkyl-5-hydroxypyrimidinone carboxamides are potent, selective HIV integrase inhibitors with good pharmacokinetic profiles in preclinical species

The dihydroxypyrimidine carboxamide 4a was discovered as a potent and selective HIV integrase strand transfer inhibitor. The optimization of physicochemical properties, pharmacokinetic profiles, and potency led to the identification of 13 in the dihydroxypyrimidine series and 18 in the N-methylpyrimidinone series having low nanomolar activity in the cellular HIV spread assay in the presence of 50% normal human serum and very good pharmacokinetics in preclinical species.