5471-82-9

Usage

Chemical Properties

Light brown crystalline powder

InChI:InChI=1/C9H9NO4/c1-6-4-3-5-7(9(11)14-2)8(6)10(12)13/h3-5H,1-2H3

Upstream product

• 186581-53-3 diazomethane 
• 5437-38-7 3-methyl-2-nitrobenzoic acid 
• 99-36-5 1-methoxycarbonyl-3-methylbenzene 
• 7697-37-2 nitric acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 99-04-7 m-Toluic acid 
• 67-56-1 methanol 
• 50424-93-6 3-methyl-2-nitrobenzoyl chloride 

Downstream Products

• 93247-78-0 methyl 1H-indole-7-carboxylate 
• 68109-89-7 methyl 3-[2-(E)-(dimethylamino)ethenyl]-2-nitro-benzoate 
• 80866-76-8 2-methyl-6-hydroxymethyl-1-nitrobenzene 
• 132874-06-7 methyl 3-(bromomethyl)-2-nitrobenzoate 
• 1038915-64-8 (3S)-3-[4-[7-(aminocarbonyl)-2H-indazol-2-yl]phenyl]piperidinium chloride 
• 1196713-67-3 2-[4-((3S)-(tertbutoxycarbonyl)piperidin-3-yl)phenyl]-2H-indazole-7-carboxylic acid methyl ester 
• 1038916-11-8 tert-butyl (3S)-3-{4-[7-(aminocarbonyl)-2H-indazol-2-yl]phenyl}piperidine-1-carboxylate 
• 138229-59-1 3-formyl-2-nitrobenzoic acid methyl ester 
• 138229-56-8 C₉H₇Br₂NO₄ 
• 1038916-08-3 2-{4-[(3S)-1-(tert-butoxycarbonyl)piperidin-3-yl]phenyl}-2H-indazole-7-carboxylic acid 
• 1312106-32-3 18-(nitrobenzylideneamino)phenylpiperidine-1-carboxylate 
• 68109-89-7 β-(dimethylamino)-3-carbomethoxy-2-nitrostyrene 
• 103441-60-7 methyl 2-iodo-3-methylbenzoate 
• 1630015-69-8 3-(3-fluoro-phenyl)-5-(2-nitro-3-methylphenyl)-1,2,4-oxadiazole 

Relevant academic research and scientific papers

Discovery and Structure-Activity Relationships of Quinazolinone-2-carboxamide Derivatives as Novel Orally Efficacious Antimalarials

A phenotypic high-throughput screen allowed discovery of quinazolinone-2-carboxamide derivatives as a novel antimalarial scaffold. Structure-activity relationship studies led to identification of a potent inhibitor 19f, 95-fold more potent than the origin

SINGLE MOLECULE COMPOUNDS PROVIDING MULTI-TARGET INHIBITION OF PARP AND OTHER PROTEINS AND METHODS OF USE THEREOF

The invention relates to compounds useful for inhibiting PARP and at least one other protein and to methods of treating diseases including cancer by administration of a compound(s) of Formula I-V (or pharmaceutically acceptable salts thereof) as defined herein.

Niraparib synthesis method

The invention discloses a Niraparib synthesis method. The method comprises that through esterification, 3-methyl hydroformylation, 3-schiff base reaction, cyclization, amidation, BOC removal and chiral resolution, optically pure Niraparib with purity of 91% or more is prepared from 3-methyl-2-nitrobenzoic acid. The method has the advantages of simple process, high efficiency, easy operation and less equipment requirement, and is a method suitable for industrial production.

Preparation method of highly selective 3-methyl-2-nitrobenzoic acid

The invention discloses a preparation method of 3-methyl-2-nitrobenzoic acid. 3-methylbenzoic acid alkyl ester is used as raw material in nitrification, two-grade selectivity and high yield are realized, and the amount of waste acid was reduced. In nitrification product, only 3-methyl 2-nitrobenzoic acid alkyl ester and 3-methyl-4-nitrobenzoic acid alkyl ester are hydrolyzed after separation to obtain 3-methyl 2-Nitrobenzoic acid and 3-methyl-4-nitrobenzoic acid. The process is simple, and suitable for industrial production.

Preparation method of 3-methoxy-2-nitrobenzoate

The invention discloses a preparation method of 3-methyl-2-nitrobenzoate. The preparation method has the advantages that firstly 3-methyl benzoate is taken as a starting material, nitrification, reduced-pressure concentration, washing with ice water, filt

One-pot synthesis of novel 3,5-disubstituted-1,2,4-oxadiazoles from indazole carboxylic acid esters and amidoximes

An efficient and high-yielding one-pot synthesis of 3,5-disubstituted-1,2, 4-oxadiazoles from indazole carboxylic acid methyl esters and amidoximes is described. In this study a series of novel 3,5-disubstituted-1,2,4-oxadiazoles (3a-d), (4a-d), (5a-d), (6a-d), (7a-d) were synthesized using amidoximes 2a-d and indazole carboxylic acid esters (3-6).

A significant improvement in enantioselectivity, yield, and reactivity for the copper-bi-o-tolyl bisoxazoline-catalyzed asymmetric allylic oxidation of cyclic olefins using recoverable SBA-15 mesoporous silica material

A series of chiral bi-o-tolyl bisoxazoline ligands 1 and 2 were conveniently synthesized on a gram scale from inexpensive and commercially available 3-methyl benzoic acid in eight steps. The catalytic and induced asymmetric effects of the chiral copper (I) complexes of these ligands on the asymmetric allylic oxidation of cycloolefins were investigated in the presence of various nano-sized additives. When SBA-15 mesoporous silica was used in conjunction with these ligands very highly enantioselectivities (up to 97% ee) and excellent yields (up to 99%) of the corresponding chiral allylic esters were obtained in a reasonably short period of time.

PHARMACEUTICALLY ACCEPTABLE SALTS OF 2-{4-[(3S)-PIPERIDIN-3- YL]PHENYL} -2H-INDAZOLE-7-CARBOXAMIDE

The present invention relates to pharmaceutically acceptable salts of an amide substituted indazole which are inhibitors of the enzyme poly(ADP-ribose)polymerase (PARP), previously known as poly(ADP-ribose)synthase and poly(ADP-ribosyl)transferase. The compounds of the present invention are useful as mono-therapies in tumors with specific defects in DNA-repair pathways and as enhancers of certain DNA -damaging agents such as anticancer agents and radiotherapy. Further, the compounds of the present invention are useful for reducing cell necrosis (in stroke and myocardial infarction), down regulating inflammation and tissue injury, treating retroviral infections and protecting against the toxicity of chemotherapy.

Design, synthesis and identification of novel colchicine-derived immunosuppressant

Synthesis and biological evaluation of various colchicine analogues through the mixed-lymphocyte reaction (MLR), lymphoproliferation, and inhibitory effects on the inflammatory genes are described. In addition, a new series of immunosuppressive agents developed on the structural basis of colchicine, as well as their structure-activity relationships is reported. The most potent analogue 20a exhibited an excellent immunosuppressive activity on in vivo skin-allograft model, which is comparable to that of cyclosporin A.

Discovery of 2-{4-[(3S)-piperidin-3-yl]phenyl}-2H-indazole-7-carboxamide (MK-4827): A novel oral poly(ADP-ribose)polymerase (PARP) inhibitor efficacious in BRCA-1 and -2 mutant tumors

We disclose the development of a novel series of 2-phenyl-2H-indazole-7- carboxamides as poly(ADP-ribose) polymerase (PARP) 1 and 2 inhibitors. This series was optimized to improve enzyme and cellular activity, and the resulting PARP inhibitors display antiproliferation activities against BRCA-1 and BRCA-2 deficient cancer cells, with high selectivity over BRCA proficient cells. Extrahepatic oxidation by CYP450 1A1 and 1A2 was identified as a metabolic concern, and strategies to improve pharmacokinetic properties are reported. These efforts culminated in the identification of 2-{4-[(3S)-piperidin-3-yl] phenyl}-2H-indazole-7-carboxamide 56 (MK-4827), which displays good pharmacokinetic properties and is currently in phase I clinical trials. This compound displays excellent PARP 1 and 2 inhibition with IC50 = 3.8 and 2.1 nM, respectively, and in a whole cell assay, it inhibited PARP activity with EC50 = 4 nM and inhibited proliferation of cancer cells with mutant BRCA-1 and BRCA-2 with CC50 in the 10-100 nM range. Compound 56 was well tolerated in vivo and demonstrated efficacy as a single agent in a xenograft model of BRCA-1 deficient cancer.