132312-86-8

Basic information

• Product Name: 2-Chloro-N-(2'-chloro-3'-pyridinyl)-3-pyridinecarboxamide
• Synonyms: 2-Chloro-N-(2'-chloro-3'-pyridinyl)-3-pyridinecarboxamide
• CAS NO: 132312-86-8
• Molecular Formula: C₁₁H₇Cl₂N₃O
• Molecular Weight: 268
• Mol File: 132312-86-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Chloro-N-(2'-chloro-3'-pyridinyl)-3-pyridinecarboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-N-(2'-chloro-3'-pyridinyl)-3-pyridinecarboxamide(132312-86-8)
• EPA Substance Registry System: 2-Chloro-N-(2'-chloro-3'-pyridinyl)-3-pyridinecarboxamide(132312-86-8)

Safety Data

• Hazardous Substances Data: 132312-86-8(Hazardous Substances Data)

Upstream product

• 6298-19-7 2-chloro-3-aminopyridine 
• 49609-84-9 2-Chloronicotinoyl chloride 
• 7440-44-0 pyrographite 

Downstream Products

• 132312-91-5 5,11-dihydro-11-<(4-methoxyphenyl)methyl>-5-methyl-6H-dipyrido<3,2-b:2',3'-e><1,4>diazepin-6-one 
• 133627-02-8 5-Cyclohexyl-10-methyl-5,10-dihydro-4,5,6,10-tetraaza-dibenzo[a,d]cyclohepten-11-one 
• 132312-46-0 5,11-dihydro-11-<(4-methoxyphenyl)methyl>-6H-dipyrido<3,2-b:2',3'-e><1,4>diazepin-6-one 
• 133627-07-3 5-Phenyl-5,10-dihydro-4,5,6,10-tetraaza-dibenzo[a,d]cyclohepten-11-one 
• 132312-45-9 N-(2-chloro-3-pyridinyl)-2-<<(4-methoxyphenyl)methyl>amino>-3-pyridinecarboxamide 

Relevant articles and documents

Synthesis and evaluation of nevirapine analogs to study the metabolic activation of nevirapine

Nevirapine (NVP) is widely used as a non-nucleoside reverse transcriptase inhibitor of HIV-1, however, it is associated with severe skin and liver injury. The mechanisms of these adverse reactions are not yet clear, but the metabolic activation of NVP is thought to be related to the injury process. Until now, several metabolic activation pathways of NVP have been reported. In this study, in order to identify the reactive metabolite of NVP mainly responsible for CYP inhibition and liver injury, we synthesized five NVP analogs designed to avoid the proposed bioactivation pathway and evaluated their metabolic stabilities, CYP3A4 time-dependent inhibitory activities, and cytotoxicity. As a result, only a pyrimidine analog of NVP, which could avoid the formation of a reactive epoxide intermediate, did not inhibit CYP3A4. Outside of this compound, the other synthesized compounds, which could avoid the generation of a reactive quinone-methide intermediate, inhibited CYP3A4 equal to or stronger than NVP. The pyrimidine analog of NVP did not induce cytotoxicity in HepG2 and transchromosomic HepG2 cells, expressing major four CYP enzymes and CYP oxidoreductase. These results indicated that the epoxide intermediate of NVP might play an important role in NVP-induced liver injury.

5,11-dihydro-6H-dipyrido(3,2-B:2',3'-E)(1,4)diazepines and their use in the prevention or treatment of HIV infection

Disclosed are novel 5,11-dihydro-6H-dipyrido[3,2-b; 2',3'-e][1,4]diazepines. These are useful in the prevention or treatment of HIV infection.

Novel Non-Nucleoside Inhibitors of HIV-1 Reverse Transcriptase. 1. Tricyclic Pyridobenzo- and Dipyridodiazepinones

Novel pyridobenzodiazepinones (I), pyridobenzodiazepinones (II), and dipyridodiazepinones (III) were found to inhibit human immunodeficiency virus type 1 (HIV-1) reverse transcriptase in vitro at concentrations as low as 35 nM.In all three series, small substituents (e.g., methyl, ethyl, acetyl) are preferred at the lactam nitrogen, whereas slightly larger alkyl moieties (e.g., ethyl, cyclopropyl) are favored at the other (N-11) diazepinone nitrogen.In general, lipophilic substituents are preferred on the A ring, whereassubstitution on the C ring generally reduces potency relative to the corresponding compounds with no substituents on the aromatic rings.Maximum potency is achieved with methyl substitution at the position ortho to the lactam nitrogen atom; however, in this case an unsubstituted lactam nitrogen is preferred.Additional substituents on the A ring can be readily tolerated.The dipyridodiazepinone derivative 11-cyclopropyl-5,11-dihydro-4-methyl-6H-dipyridodiazepin-6-one (96, nevirapine) is a potent (IC50 = 84 nM) and selective non-nucleoside inhibitor of HIV-1 reverse transcriptase, and has been chosen for clinical evaluation.