606-18-8

Usage

Chemical Properties

Yellow Solid

InChI:InChI=1/C7H6N2O4/c8-6-4(7(10)11)2-1-3-5(6)9(12)13/h1-3H,8H2,(H,10,11)/p-1

Upstream product

• 209899-26-3 2-ethoxy-3-nitro-benzoic acid ethyl ester 
• 77326-45-5 2-carbamoyl-3-nitrobenzoic acid 
• 89375-28-0 8-nitro-2H-benzo[d][1,3]oxazine-2,4(1H)-dione 
• 121-92-6 3-nitrobenzoic acid 
• 641-70-3 3-nitrophthalic acid anhydride 
• 7664-93-9 sulfuric acid 
• 7664-41-7 ammonia 
• 3970-35-2 2-chloro-3-nitrobezoic acid 
• 570-24-1 2-Methyl-6-nitroaniline 
• 603-11-2 3-nitrophthalic acid 
• 90417-80-4 2-acetylamino-3-nitro-benzoic acid 
• 603-62-3 4-nitro-1H-isoindole-1,3(2H)-dione 
• 88-74-4 2-nitro-aniline 
• 17122-60-0 2-(N-hydroxyimino)-N-(2-nitrophenyl)acetamide 

Downstream Products

• 57113-91-4 methyl 3-nitroanthranilate 
• 53638-54-3 8-nitroquinazolin-4-ol 
• 669070-81-9 2-amino-3-cyclohexylamino-benzoic acid methyl ester 
• 1134349-99-7 2-amino-N-isopropyl-3-nitrobenzamide 
• 1309042-20-3 (L)-2-(pyridin-2-yl)-N-(1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl)-1H-benzimidazole-4-carboxamide 
• 1309042-22-5 (L)-2-(pyridin-3-yl)-N-(1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl)-1H-benzimidazole-4-carboxamide 
• 1309042-24-7 (L)-2-(pyridin-4-yl)-N-(1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl)-1H-benzimidazole-4-carboxamide 
• 1160269-67-9 2-(furan-2-yl)-N-(2-fluorophenyl)-1H-benzimidazole-4-carboxamide 
• 1309042-26-9 (L)-2-(furan-2-yl)-N-(1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl)-1H-benzimidazole-4-carboxamide 
• 266993-72-0 3-carbamoylbenzene-1,2-diaminium dichloride 
• 1346644-95-8 C₁₅H₂₁N₃O₂S₂ 
• 98451-51-5 2-amino-6-nitrobenzyl alcohol 
• 130133-53-8 2-amino-6-nitrobenzaldehyde 
• 904817-12-5 2-(2-hydroxyphenyl)-1H-benzo[d]imidazole-7-carboxylic acid 

Relevant academic research and scientific papers

Synthesis and evaluation of 2-(4-[4-acetylpiperazine-1-carbonyl] phenyl)-1H-benzo[d]imidazole-4-carboxamide derivatives as potential PARP-1 inhibitors and preliminary study on structure-activity relationship

Although 1H-benzo[d]imidazole-4-carboxamide derivatives have been explored for a long time, the structure–activity relationship of the substituents in the hydrophobic pocket (AD binding sites) has not thoroughly discovered. Here in, a series of 2-(4-[4-acetylpiperazine-1-carbonyl]phenyl)-1H-benzo[d]imidazole-4-carboxamide derivatives have been designed, synthesized, and successful characterization as novel and effective poly ADP-ribose polymerases (PARP)-1 inhibitors to improve the structure–activity relationships about the substituents in the hydrophobic pocket. These derivatives were evaluated for their PARP-1 inhibitory activity and cellular inhibitory against BRCA-1 deficient cells (MDA-MB-436) and wild cells (MCF-7) using PARP kit assay and MTT method. The results indicated that compared with other heterocyclic compounds, furan ring-substituted derivatives 14n-14q showed better PARP-1 inhibitory activity. Among this derivatives, compound 14p displayed the strongest inhibitory effects on PARP-1 enzyme (IC50?=?0.023 μM), which was close to that of Olaparib. 14p (IC50?=?43.56 ± 0.69 μM) and 14q (IC50?=?36.69 ± 0.83 μM) displayed good antiproliferation activity on MDA-MB-436 cells and inactivity on MCF-7 cells, indicating that 14p and 14q have high selectivity and targeting. The molecular docking method was used to explore the binding mode of compound 14p and PARP-1, and implied that the formation of hydrogen bond was essential for PARP-1 inhibition activities. This study also showed that in the hydrophobic pocket (AD binding sites), the introduction of strong electronegative groups (furan ring, e.g.) or halogen atoms in the side chain of benzimidazole might improve its inhibitory activity and this strategy could be applied in further research.

Synthesis and pharmacological evaluation of N-benzyl substituted 4-bromo-2,5-dimethoxyphenethylamines as 5-HT2A/2C partial agonists

N-Benzyl substitution of phenethylamine 5-HT2A receptor agonists has dramatic effects on binding affinity, receptor selectivity and agonist activity. In this paper we examine how affinity for the 5-HT2A/2C receptors are influenced by N-benzyl substitution of 4-bromo-2,5-dimethoxyphenethylamine derivatives. Special attention is given to the 2′ and 3′-position of the N-benzyl as such compounds are known to be very potent. We found that substitutions in these positions are generally well tolerated. The 2′-position was further examined using a range of substituents to probe the hydrogen bonding requirements for optimal affinity and selectivity, and it was found that small changes in the ligands in this area had a profound effect on their affinities. Furthermore, two ligands that lack a 2′-benzyl substituent were also found to have high affinity contradicting previous held notions. Several high-affinity ligands were identified and assayed for functional activity at the 5-HT2A and 5-HT2C receptor, and they were generally found to be less efficacious agonists than previously reported N-benzyl phenethylamines.

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.

1H-PYRAZOLO[3,4-B]PYRIDINES AND THERAPEUTIC USES THEREOF

Provided herein are compounds according to Formulas (I) or (II) and pharmaceutically acceptable salts thereof, and compositions comprising the same, for use in various methods, including treating cancer, abnormal cellular proliferation, angiogenesis, Alzheimer's disease, lung disease, osteoarthritis, idiopathic pulmonary fibrosis and neurological conditions/disorders/diseases.

Benzimidazole-4-Carboxamide Derivatives, Their Preparation Methods, Pharmaceutical Compositions And Their Uses

The present invention relates to the benzimidazole-4-carboxamide derivatives, their preparation methods, pharmaceutical compositions and their uses; wherein X represents monosubstituted or bissubstituted or polysubstitued C1-C14 alkoxy, monosubstituted or bisubstituted or polysubstitued C1-C14 alkyl, monosubstituted or bisubstituted or polysubstitued C2-C14 alkenyl, monosubstituted or bisubstituted or polysubstitued C6-C14 aryl, or monosubstituted or bisubstituted or polysubstitued 5 to 6 membered heterocyclic group, or monosubstituted or bisubstituted or polysubstitued fused ring group containing nitrogen heteroatom; Y represents hydrogen, monosubstituted or bisubstituted or polysubstitued C1-C16 alkyl, monosubstituted or bisubstituted or polysubstitued C6-C12 aryl, or monosubstituted or bisubstituted or polysubstitued 5 to 6 membered heterocyclic group, or monosubstituted or bisubstituted or polysubstitued fused ring group containing nitrogen heteroatom. The derivatives of the present invention have the functions of antiviral medicine.

Inhibitory properties of 2-substituent-1H-benzimidazole-4-carboxamide derivatives against enteroviruses

A series of novel benzimidazole derivatives were designed, synthesized, and evaluated for their activities against four kinds of enteroviruses, that is, Coxsackie virus A16, B3, B6 and Enterovirus 71 in VERO cells. Strong activities against enterovirus replication and low cytotoxicities were observed in these benzimidazoles generally. The most promising compound was (l)-2-(pyridin-2-yl)- N-(2-(4-nitrophenyl)pentan-3-yl)-1H-benzimidazole-4-carboxamide (16), with a high antiviral potency (IC50 = 1.76 μg/mL) and a remarkable selectivity index (328). These compounds were selected for further evaluation as novel enterovirus inhibitors.

LIPOIC ACID AND NITROXIDE DERIVATIVES AND USES THEREOF

The present invention provides bifunctional compounds comprising a poly(ADP-ribose) polymerase (PARP) inhibitor moiety and a reactive oxygen species (ROS) scavenger moiety, more particularly, a lipoic acid or cyclic nitroxide derivative, covalently attached either directly or via a linker, as well as pharmaceutical compositions comprising them. The compounds and pharmaceutical compositions of the invention are useful for prevention, treatment, or management of diseases, disorders and conditions associated with elevated PARP activity or expression.

Copper-catalyzed direct amination of ortho-functionalized haloarenes with sodium azide as the amino source

A simple copper-catalyzed direct amination of ortho-functionalized haloarenes (2-halobenzoic acid, 2-halobenzamide, and N-(2-bromophenyl)acetamide derivatives) has been developed with use of NaN3 as the amino source in ethanol, and the corresponding ortho-functionalized aromatic amines were synthesized in good to excellent yields. The protocol undergoes one-pot Ullmann-type coupling of ortho-functionalized haloarenes with NaN3 to lead to ortho-functionalized azidoarenes, followed by reduction with ethanol.

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.