13253-57-1

Upstream product

• 6973-60-0 1-Methyl-2-pyrrolecarboxylic acid 
• 95-54-5 1,2-diamino-benzene 
• 96-54-8 N-Methylpyrrole 
• 54624-57-6 2-bromo-1H-1,3-benzodiazole 
• 4857-06-1 2-chloro-1H-benzoimidazole 
• 1192-58-1 N-methylpyrrole aldehyde 

Downstream Products

• 1081112-15-3 2-(1-methylpyrrol-2-yl)-1-{3-[4-(3-acetamidophenyl)piperidin-1-yl]propyl}-1H-benzimidazole 
• 1467028-82-5 (2S)-N-{4-(3-[2-(1-methyl-2-pyrrolyl)benzimidazol-1-yl]pentyl)oxy-5-methoxy-2-nitrobenzoyl}pyrrolidine-2-carboxaldehyde diethyl thioacetal 
• 1467028-86-9 (2S)-N-{4-(3-[2-(1-methyl-2-pyrrolyl)benzimidazol-1-yl]pentyl)oxy-5-methoxy-2-aminobenzoyl}pyrrolidine-2-carboxaldehyde diethyl thioacetal 
• 1187383-59-0 C₃₂H₃₉N₅O₅S₂ 

Relevant academic research and scientific papers

Synthesis of Arylated Nucleobases by Visible Light Photoredox Catalysis

Arylated nucleobases were synthesized by visible light photocatalysis using rhodamine 6G as photoredox catalyst and N,N-diisopropylethylamine as sacrificial electron donor. The high redox potential of this catalyst system is achieved by a consecutive photoinduced electron transfer process (conPET) and allows the room temperature conversion of brominated and chlorinated nucleobases or nucleobase precursors as starting materials. In contrast to many transition-metal-based syntheses, a direct C-H arylation of nitrogen-containing halogenated heterocycles is possible without protection of the N-H groups. The method provides a simple, metal-free alternative for the synthesis of biologically interesting arylated heterocycles under mild conditions.

Metal-Free Photocatalyzed Cross Coupling of Bromoheteroarenes with Pyrroles

The excited radical anion of rhodamine 6G reduces heteroaryl bromides and chlorides to generate heteroaryl radicals that were successively trapped by pyrroles for the synthesis of heteroaromatic biaryls in moderate to excellent yields. The synthetically important photoredox catalytic C-H heteroarylation reaction works for a broad range of brominated electron-rich heteroarenes and chlorinated heteroarenes bearing electron withdrawing groups. In addition, this methodology was applied to the formal synthesis of a benzimidazole derivative II with interesting pharmacological properties.

RESEARCH ON THE CHEMISTRY OF 2-HETARYLBENZIMIDAZOLES. 2. SYNTHESIS AND PROPERTIES OF 1-METHYL-2-(1'-METHYL-2'-PYRROLYL)BENZIMIDAZOLE

The condensation of 1-methyl-2-formylpyrrole with o-phenylenediamine gave 2-(1'-methyl-2'-pyrrolyl)benzimidazole, which was subjected to methylation.The alkylation product was subjected to electrophilic substitution.The substituent is incorporated in the 4 or 5 position of the hetaryl ring; however, bromination of 1-methyl-2-(1'-methyl-2'-pyrrolyl)benzimidazole leads to the formation of the mono-, di-, and tribromo derivatives, depending on the conditions.The acidophobic properties of the pyrrole ring are partially lost as a consequence of the effect of the benzimidazole ring.

peri-Xanthenoxanthene (PXX): a Versatile Organic Photocatalyst in Organic Synthesis

Recent years have witnessed a continuous development of photocatalysts to satisfy the growing demand of photophysical and redox properties in photoredox catalysis, with complex structures or alternative strategies devised to access highly reducing or oxidising systems. We report herein the use of peri-xanthenoxanthene (PXX), a simple and inexpensive dye, as an efficient photocatalyst. Its highly reducing excited state allows activation of a wide range of substrates, thus triggering useful radical reactions. Benchmark transformations such as the addition of organic radicals, generated by photoreduction of organic halides, to radical traps are initially demonstrated. More complex dual catalytic manifolds are also shown to be accessible: the β-arylation of cyclic ketones is successful when using a secondary amine as organocatalyst, while cross-coupling reactions of aryl halides with amines and thiols are obtained when using a Ni co-catalyst. Application to the efficient two-step synthesis of the expensive fluoro-tetrahydro-1H-pyrido[4,3-b]indole, a crucial synthetic intermediate for the investigational drug setipiprant, has been also demonstrated. (Figure presented.).

A practical green synthesis and biological evaluation of benzimidazoles against two neglected tropical diseases: Chagas and leishmaniasis

Antimicrobial resistance is an ever-increasing problem throughout the world and has already reached severe proportions. Two very common neglected tropical diseases are Chagas' disease and leishmaniasis. Chagas' disease is a severe health problem, mainly in Latin America, causing approximately 50000 deaths a year and millions of people are infected. About 25-30% of the patients infected with Trypanosoma cruzi develop the chronic form of the disease. On the other hand, Leishmaniasis represents complex diseases with an important clinical and epidemiological diversity. It is endemic in 88 countries 72 of which are developing countries and it has been estimated that are 12 million people infected and 350 million are in areas with infection risk. On this basis, research on organic compounds that can be used against these two diseases is an important target. A very simple, green, and efficient protocol is developed in which bismuth nitrate pentahydrate is employed as a Lewis acid catalyst in aqueous media under microwave irradiation for the synthesis of various 2-aryl substituted benzimidazoles from aldehydes and o-phenylenediamine. Other salient features of this protocol include milder conditions, atom-economy, easy extraction, and no wastes. Nine 1H-benzimidazole derivatives (1-9) with substituents at positions 2 and 5 were synthesized and the structure of the compounds was elucidated by spectroscopic methods. The compounds were screened to identify whether they posses pharmacological activity against Chagas' disease and leishmaniasis. Compound 8 showed better activity than the control Nifurtimox against INC-5 Trypanosoma cruzi strain whereas compounds 3 and 9 have demonstrated potent leshmanicidal activity. A systematic green synthetic procedure and in vitro biological evaluation of nine 1H-benzimidazoles are described.

Synthesis, DNA binding ability and anticancer activity of 2-heteroaryl substituted benzimidazoles linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates

As a continuation of our efforts to develop the benzimidazole-PBD conjugates as potential anticancer agents, a series of heteroaryl substituted benzimidazole linked PBD conjugates has been synthesized and evaluated for their anticancer potential in 60 human cancer cell lines. Most of the compounds exhibited promising anticancer activity and interestingly, compounds 4c and 4d displayed significant activity in most of the cell lines tested. Whereas, compound 4e showed selectivity in renal cancer cells with GI50 values of 10 and 70 nM against RXF 393 and UO-31 cell lines, respectively. Further, these compounds also showed significant DNA-binding affinity by thermal denaturation study using duplex form of calf thymus (CT) DNA.

2-heteroaryl benzimidazole derivatives as melanin concentrating hormone receptor 1 (MCH-R1) antagonists

A novel series of 2-heteroaryl substituted benzimidazole derivatives, containing the piperidinylphenyl acetamide group at the 1-position, were synthesized and evaluated as MCH-R1 antagonists. Extensive SAR investigation probing the effects of C-2 heteroaryl group led to the identification of 2-[2-(pyridin-3-yl)ethyl] analog 3o, which exhibits highly potent MCH-R1 binding activity with an IC50 value of 1 nM. This substance 3o also has low hERG binding activity, good metabolic stability, and favorable pharmacokinetic properties.