57113-91-4

Usage

Chemical Properties

Yellow Solid

Uses

An intermediate in the preparation of Candesartan.

InChI:InChI=1/C8H8N2O4/c1-14-8(11)5-3-2-4-6(7(5)9)10(12)13/h2-4H,9H2,1H3

Upstream product

• 606-18-8 3-nitroanthranilic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 134-20-3 2-carbomethoxyaniline 
• 186581-53-3 diazomethane 
• 136918-14-4 phthalimide 
• 96385-50-1 3-nitrophthalamide 
• 112656-95-8 7-nitroindoline-2,3-dione 
• 88-74-4 2-nitro-aniline 
• 17122-60-0 2-(N-hydroxyimino)-N-(2-nitrophenyl)acetamide 
• 77-78-1 dimethyl sulfate 
• 856414-36-3 2-Azidocarbonyl-3-nitro-benzoic acid methyl ester 
• 77326-45-5 2-carbamoyl-3-nitrobenzoic acid 
• 2719-08-6 methyl 2-(acetylamino)benzoate 
• 95067-27-9 2-acetylamino-3-nitro-benzoic acid methyl ester 

Downstream Products

• 107582-20-7 2,3-diaminobenzoic acid methyl ester 
• 313278-90-9 methyl 2-N-(trifluoroacetyl)amino-3-nitrobenzoate 
• 212503-82-7 methyl N,N-bis(2,6-difluorobenzoyl)-3-nitro-2-anilinecarboxylate 
• 212503-83-8 methyl N-(2,6-difluorobenzoyl)-3-nitro-2-anilinecarboxylate 
• 327619-43-2 2,6-difluorobenzoic acid 2-hydroxymethyl-6-nitroanilide 
• 327619-44-3 2,6-difluorobenzoic acid 2-acetoxymethyl-6-nitroanilide 
• 212503-84-9 methyl 2-(2,6-difluorophenyl)-benzimidazole-2-carboxylate 
• 327619-45-4 2-(2,6-difluorophenyl)-4-acetoxymethylbenzimidazole 
• 212503-86-1 methyl 1-(2,6-difluorobenzyl)-2-(2,6-difluorophenyl)-benzimidazole-2-carboxylate 
• 212503-33-8 1-(2,6-difluorobenzyl)-2-(2,6-difluorophenyl)-4-cyano-benzimidazole 
• 212503-87-2 1-(2,6-difluorobenzyl)-2-(2,6-difluorophenyl)-benzimidazole-2-carboxylate 
• 327619-55-6 N-1-(2,6-difluorobenzyl)-2-(2,6-difluorophenyl)-benzimidazol-4-methyl-acetamide 
• 327619-53-4 1-(2,6-difluorobenzyl)-2-(2,6-difluorophenyl)-4-chloromethylbenzimidazole 
• 327619-54-5 1-(2,6-difluorobenzyl)-2-(2,6-difluorophenyl)-4-methyleneazidobenzimidazole 

Relevant academic research and scientific papers

Method for preparing 2-amino-3-methyl nitrobenzoate

The invention discloses a method for preparing methyl 2-amino-3-nitrobenzoate, which comprises the following steps: pumping a phthalimide solution and a sodium hypochlorite solution into a micro-reaction mixer, reacting, reacting with water in a tubular reactor to obtain methyl anthranilate, and continuously separating to obtain a crude product; pumping the methyl anthranilate crude product, an acetic anhydride solution and fuming nitric acid into a micro-channel reactor, mixing, reacting to obtain N-methyl nitrobenzoate, and continuously separating to obtain a crude product; pumping an N-methyl nitrobenzoate solution, concentrated sulfuric acid and water into a micro-channel reactor, mixing, and reacting to obtain a 2-amino-3-methyl nitrobenzoate crude product; recrystallizing the crude product in methanol to obtain a product, namely methyl 2-amino-3-nitrobenzoate; and the method is high in yield, good in safety and suitable for industrial production.

Identification and development of non-cytotoxic cell death modulators: Impact of sartans and derivatives on PPARγ activation and on growth of imatinib-resistant chronic myelogenous leukemia cells

4’-((2-Propyl-1H-benzo[d]imidazol-1-yl)methyl)-[1,1′-biphenyl]-2-carboxylic acid derived from telmisartan was identified as lead for the design of cell death modulators. In this study, we evaluated the efficacy of telmisartan itself and other sartans in combination with imatinib against K562-resistant cells. The findings were directly used to further optimize the lead structure. Telmisartan and candesartan cilexetil represented the most effective sartans, thus the influence of carboxyl/methyl carboxylate groups at positions 7 (compounds 6, 7) or 4 (compounds 12–14) at the benzimidazole core was studied. Additionally, according to the results of a former structure-activity study, telmisartan was transformed to the related amide (1). Telmisartan amide 1, as well as the esters 6 and 12 markedly sensitized the resistant CML cells to imatinib treatment. Correlation with their potency to activate PPARγ is not given. Candesartan cilexetil, telmisartan and 1 showed the profile of partial agonists at PPARγ with EC50 values of 4.2, 4.3 and 9.1 μM, respectively, while 6 and 12 caused only marginal intrinsic activation at 10 μM (Amax = 22% and 13%). However, the repression of the STAT5 phosphorylation relates with the possibility to sensitize K562-resistant CML cells to imatinib treatment. It is worth mentioning that all compounds were per se non-cytotoxic at relevant concentrations.

A 2 - ethoxy benzimidazole - 7 - carboxylic acid methyl ester

The invention discloses a synthesis method of 2-ethoxy benzimidazole-7-carboxylic acid methyl ester. The problem that an existing process is not high in content and is very low in yield is solved. According to the synthesis method, 3-nitryl phthalic acid is used as a raw material, rearrangement is performed in a water solution after methyl esterification, acylation and re-nitridation, then tin powder is adopted to perform reduction and loop closing so as to obtain the 2-ethoxy benzimidazole-7-carboxylic acid methyl ester. By the adoption of the synthesis method, produced impurities are very little, the content is high, and the yield is also high.

The discovery of new scaffold of plant activators: From salicylic acid to benzotriazole

Started from salicylic acid (SA) and related commercialized plant activators, based on molecular three-dimensional shape and pharmacophore similarity comparison (SHAFTS), a new lead compound benzotriazole was predicted and a series of benzotriazole derivatives were designed and synthesized. The bioassay showed that benzotriazole had high activity against a broad spectrum of diseases including fungi and oomycetes in vivo, but no activity in vitro. And the introduction of proper groups at the 1’-position and 5’-position was beneficial to the activity. So, they had the potential to be exploited as novel plant activators.

ANTI-MALIGNANT TUMOR AGENT COMPOSITION

To provide a satisfactory anticancer agent composition suppressing the growth of cancer (malignant tumor) reliably and hardly causing side effects, the present invention is directed to an anticancer agent composition including the following agents as active ingredient; a LAT1 inhibitor, and one or more agents selected from the group consisting of an alkylating agent, a platinum-based antineoplastic agent, an anti-metabolite, a topoisomerase inhibitor, an anti-microtubule polymerizing agent, a hormonal agent, an anti-microtubule depolymerizing agent, an anticancer antibiotic, and a molecular targeted agent.

Catalytic formation of ketones from unactivated esters through rhodium chelation-assisted C-O bond activation

A new method for building aryl aryl ketones containing heterocyclic rings through chelation-assisted C-O bond activation catalyzed by a rhodium complex has been developed. In this reaction, methyl quinoline-8-carboxylate, methyl quinoxaline-5-carboxylate, and their derivatives were reacted with an excess amount of a substituted phenyl boronic acid in the presence of a rhodium(I) complex to give substituted phenyl(quinolin-8-yl)methanone, phenylquinoxalin-5- ylmethanone, and their derivatives in medium to high yields. The current method offers a highly favorable synthetic pathway to efficiently build related drugs with an 8-benzoylquinoline core structure. This method may prove especially valuable for medicinal chemists for the late-stage introduction of versatile ketone moieties into complex scaffolds for diversity-oriented synthetic strategies.

SUBSTITUTED BENZIMIDAZOLES, BENZOTHIAZOLES AND BENZOXAZOLES

The present invention relates to substituted benzimidazoles, benzothiazoles and benzoxazoles, processes for their preparation, medicaments containing these compounds and the use of these compounds for the preparation of medicaments.

DIHYDROOROTATE DEHYDROGENASE INHIBITORS

The invention relates to compounds of formula (I) wherein R1, R2, X1, X2, Y, Ra, Rb, Q have the meanings given in claim 1. The compounds are useful e.g. in the treatment of autoimmune disorders, such as multiple sclerosis and also in the treatment of cancer disorders.

New practical synthesis of the key intermediate of candesartan

The development of a new, practical synthesis of methyl 3-amino-N-(2′-cyanobiphenyl-4-yl)methyl]anthranilate, key intermediate of candesartan, is described, starting from methyl anthranilate. The features of our approach are as follows: (i) introduction of the 3-nitro group by acid catalysed rearrangement of the corresponding methyl N-nitroanthranilate; (ii) introduction of a (2′-cyanobiphenyl-4-yl)methyl side chain by N-alkylation of the appropriate N-nitroanthranilic acid derivative. In the most efficient procedure methyl N,3-dinitroanthranilate was N-alkylated with 4′-bromomethyl-biphenyl-2-nitrile. Catalytic reduction of the aromatic nitro group was accompanied with the removal of the N-nitro function to afford the required key intermediate in good yield.

SUBSTITUTED DIHYDROPYRIDINES AND METHODS OF USE

Compounds are provided that are modulators of the C5a receptor. The compounds are substituted dihydropyridines and are useful in pharmaceutical compositions, methods for the treatment of diseases and disorders involving the pathologic activtation of C5a receptors.