70733-25-4

Upstream product

• 827-24-7 2-bromo-4-methyl-6-nitroaniline 
• 449790-63-0 2-bromo-4-methyl-6-nitrophenyl azide 
• 103-89-9 4-Methylacetanilide 
• 40371-61-7 N-(3-bromo-4-methyl-phenyl)acetamide 
• 89-62-3 4-methyl-2-nitroaniline 
• 62827-39-8 3-Bromo-5-nitro-p-toluidine 

Downstream Products

• 116222-29-8 4-Nitro-benzoic acid N'-(9-bromo-3-hydroxy-7-methyl-4-undecyl-phenazin-2-yl)-hydrazide 
• 116222-35-6 10-Bromo-8-methyl-3-(4-nitro-phenyl)-5-undecyl-1H-4-oxa-1,2,6,11-tetraaza-naphthacene 
• 1126824-09-6 4-bromo-6-methyl-1H-benzo[d]imidazole 
• 1257655-43-8 C₂₁H₁₇BrN₂O₂ 
• 1123738-34-0 C₂₀H₂₂N₄ 
• 1092500-71-4 8-bromo-6-methyl-2-(3,4,5-trimethoxy-phenyl)-quinoxaline 
• 70733-29-8 7-Bromo-5-methyl-4-nitrobenzo-2,1,3-thiadiazol 

Relevant academic research and scientific papers

Synthesis of 4,4′-bisaryl-2,2′-bisbenzimidazoles as building blocks for supramolecular structures

(Chemical Equation Presented) A series of 4,4′-bisaryl-2,2′- bisbenzimidazoles has been synthesized from the corresponding 4,4′-dibromo-2,2′-bisbenzimidazoles by Negishi coupling reactions. This procedure affords highly substituted bisbenzimidazoles.

Synthesis and evaluation of novel and potent protease activated receptor 4 (PAR4) antagonists based on a quinazolin-4(3H)-one scaffold

Protease activated receptor 4 (PAR4) is an important target in antiplatelet therapy to reduce the risk of heart attack and thrombotic complications in stroke. PAR4 antagonists can prevent harmful and stable thrombus growth, while retaining initial thrombus formation, by acting on the late diffusion stage of platelet aggregation, and may provide a safer alternative to other antiplatelet agents. To date, only two PAR4 antagonists, BMS-986120 and BMS-986141 have entered clinical trials for thrombosis. Thus, the development of a potent and selective PAR4 antagonist with a novel chemotype is highly desirable. In this study, we explored the activity of quinazolin-4(3H)-one-based PAR4 antagonists, beginning with their IDT analogues. By repeated structural optimisation, we developed a series of highly selective PAR4 antagonists with nanomolar potency on human platelets. Of these, 13 and 30g, with an 8-benzo[d]thiazol-2-yl-substituted quinazolin-4(3H)-one structure, showed optimal activity (h. PAR4-AP PRP IC50 = 19.6 nM and 6.59 nM, respectively) on human platelets. Furthermore, 13 and 30g showed excellent selectivity for PAR4 versus PAR1 and other receptors (IC50s > 10 μM) on human platelets. And 13 and 30g were lack of cross-reactivity for PAR1 or PAR2 (PAR1 AP FLIPR IC50 > 3162 nM, PAR2 AP FLIPR IC50 > 1000 nM) in the calcium mobilization assays. Metabolic stability assays and cytotoxicity tests of 13 and 30g indicated that these compounds could sever as promising drug candidates for the development of novel PAR4 antagonists. In summary, the quinazolin-4(3H)-one-based analogues are the first reported chemotypes with excellent activity and selectivity against PAR4, and, in the current study, we expanded the structural diversity of PAR4 antagonists. The two compounds, 13 and 30g, found in our study could be promising starting points with great potential for further research in antiplatelet therapy.

TYK2 INHIBITORS AND USES THEREOF

Described herein are compounds that are useful in treating a TYK2-mediated disorder. In some embodiments, the TYK2-mediated disorder is an autoimmune disorder, an inflammatory disorder, a proliferative disorder, an endocrine disorder, a neurological disorder, or a disorder associated with transplantation.

A Common, Facile and Eco-Friendly Method for the Reduction of Nitroarenes, Selective Reduction of Poly-Nitroarenes and Deoxygenation of N-Oxide Containing Heteroarenes Using Elemental Sulfur

A transition metal-free, environment-friendly and practical protocol was developed either for the reduction of nitroarenes or for the deoxygenation of N-oxide containing heteroarenes. The reaction proceeded with the use of a non-toxic and cheap feedstock as elemental sulfur in aqueous methanol under relatively mild conditions. Green chemistry credentials were widely favorable compared to traditional and industrial protocols with good E-factors and a low production of waste. The strategy allowed the efficient reduction of a large variety of substituted-nitroarenes including various o-nitroanilines as well as selective reduction of various poly-nitroarenes in excellent yields with a broad substrate scope. The protocol was successfully extended to the deoxygenation of some N-oxide containing heteroarenes, like benzofuroxans, phenazine N,N'-dioxides, pyridine N-oxides, 2H-indazole N1-oxides, quinoxaline N1,N4-dioxides and benzo[d]imidazole N1,N3-dioxides. A gram-scale example for the synthesis of luminol, in green conditions, was reported. A solid mechanism of reaction was proposed from experimental evidences.

Substituted benzimidazoles as modulators of Ras signaling

Benzimidazole compounds that increase the rate of SOS-mediated nucleotide exchange on Ras by binding to a functionally relevant, chemically tractable pocket on the SOS protein, as part of the Ras:SOS:Ras complex.

TRICYCLIC HETEROARYL-SUBSTITUTED QUINOLINE AND AZAQUINOLINE COMPOUNDS AS PAR4 INHIBITORS

Disclosed are compounds of Formula (I) to (VIII): (I) (II) (III) (IV) (V) (VI) (VII) (VIII) or a stereoisomer, tautomer, pharmaceutically acceptable salt, solvate or prodrug thereof, wherein R3 is a tricyclic heteroaryl group substituted with R3a and zero to 2 R3b; and R1, R2, R3a, R3b, R4, and n are defined herein. Also disclosed are methods of using such compounds as PAR4 inhibitors, and pharmaceutical compositions comprising such compounds. These compounds are useful in inhibiting or preventing platelet aggregation, and are useful for the treatment of a thromboembolic disorder or the primary prophylaxis of a thromboembolic disorder.

BICYCLIC HETEROARYL SUBSTITUTED COMPOUNDS

Disclosed are compounds of Formula (I) to (VIII): (I) (II) (III) (IV) (V) (VI) (VII) (VIII); or a stereoisomer, tautomer, pharmaceutically acceptable salt, solvate or prodrug thereof, wherein R3 is a bicyclic heteroaryl group substituted with zero to 3 R3a; and R1, R2, R3a, R4, and n are defined herein. Also disclosed are methods of using such compounds as PAR4 inhibitors, and pharmaceutical compositions comprising such compounds. These compounds are useful in inhibiting or preventing platelet aggregation, and are useful for the treatment of a thromboembolic disorder or the primary prophylaxis of a thromboembolic disorder.

Heterocyclic Systems Containing Bridgehead Nitrogen Atom: Part XXXIX - Reaction of 2-Mercapto-4-bromo-6-methylbenzimidazole with Chloroacetic Acid and 1,2-Dibromoethane

8-Bromo-6-methylthiazolobenzimidazol-3(2H)-one (IVa) and 8-bromo-6-methyl-2,3-dihydrothiazolobenzimidazole (V) have been synthesized starting from 2-mercapto-4-bromo-6-methylbenzimidazole (II), prepared by the reaction of 3-bromo-5-methyl-1,