10597-52-1Relevant articles and documents
Catalytic synthesis of benzimidazoles and organic carbamates using a polymer supported zinc catalyst through CO2 fixation
Biswas, Imdadul Haque,Biswas, Surajit,Islam, Md Sarikul,Riyajuddin, Sk,Sarkar, Priyanka,Ghosh, Kaushik,Islam, Sk Manirul
, p. 14643 - 14652 (2019)
Utilization of carbon dioxide in chemical fixation for synthesis of fine chemicals like benzimidazoles, organic carbamates, etc. is in high demand in recent years as carbon dioxide is a cost effective, sustainable, and green renewable C1 source. In this article we present the design and synthesis of an organically modified polystyrene bound heterogeneous [PS-Zn(ii)-SALTETA] catalyst. The catalyst has been characterized thoroughly by Fourier transform infrared spectroscopy, atomic absorption spectroscopy, thermo gravimetric analysis, PXRD, SEM and EDAX studies. The catalyst was used for cyclization of o-phenylenediamines through insertion of carbon dioxide in order to produce benzimidazoles in the presence of dimethylamine borane (DMAB). The developed catalytic procedure is sustainable, economical and efficient owing to the utilization of ethanol/water as a biodegradable and environment friendly solvent system. Besides benzimidazole production the catalyst was also very active for manufacture of organic carbamates from anilines and n-butyl bromide under atmospheric CO2 pressure under solvent free conditions at room temperature and the catalytic protocol showed outstanding functional group tolerance. Moreover the catalyst is highly recyclable and reusable.
Metal-Free Synthesis of Benzimidazoles via Oxidative Cyclization of d -Glucose with o-Phenylenediamines in Water
Raja, Dineshkumar,Philips, Abigail,Palani, Pushbaraj,Lin, Wei-Yu,Devikala, Sundaramurthy,Senadi, Gopal Chandru
, p. 11531 - 11540 (2020)
d-Glucose has been identified as an efficient C1 synthon in the synthesis of benzimidazoles from o-phenylenediamines via an oxidative cyclization strategy. Isotopic studies with 13C6-d-glucose and D2O unambiguously confirmed the source of methine. The notable features of this method include the following: broad functional group tolerance, a biorenewable methine source, excellent reaction yields, a short reaction time, water as an environmentally benign solvent, and the synthesis of vitamin B12 component on the gram scale.
Base substituted 5′-O-(N-isoleucyl)sulfamoyl nucleoside analogues as potential antibacterial agents
Gadakh, Bharat,Vondenhoff, Gaston,Lescrinier, Eveline,Rozenski, Jef,Froeyen, Mathy,Van Aerschot, Arthur
, p. 2875 - 2886 (2014)
Aminoacyl-sulfamoyl adenosines are well-known nanomolar inhibitors of the corresponding prokaryotic and eukaryotic tRNA synthetases in vitro. Inspired by the aryl-tetrazole containing compounds of Cubist Pharmaceuticals and the modified base as found in the natural antibiotic albomycin, the selectivity issue of the sulfamoylated adenosines prompted us to investigate the pharmacophoric importance of the adenine base. We therefore synthesized and evaluated several isoleucyl-sulfamoyl nucleoside analogues with either uracil, cytosine, hypoxanthine, guanine, 1,3-dideaza-adenine (benzimidazole) or 4-nitro-benzimidazole as the heterocyclic base. Based on the structure and antibacterial activity of microcin C, we also prepared their hexapeptidyl conjugates in an effort to improve their uptake potential. We further compared their antibacterial activity with the parent isoleucyl-sulfamoyl adenosine (Ile-SA), both in in vitro and in cellular assays. Surprisingly, the strongest in vitro inhibition was found for the uracil containing analogue 16f. Unfortunately, only very weak growth inhibitory properties were found as of low uptake. The results are discussed in the light of previous literature findings.
Synthesis and evaluation of analogs of 5′-(((Z)-4-amino-2-butenyl)methylamino)-5′-deoxyadenosine (MDL 73811, or AbeAdo) – An inhibitor of S-adenosylmethionine decarboxylase with antitrypanosomal activity
Brockway, Anthony J.,Volkov, Oleg A.,Cosner, Casey C.,MacMillan, Karen S.,Wring, Stephen A.,Richardson, Thomas E.,Peel, Michael,Phillips, Margaret A.,De Brabander, Jef K.
, p. 5433 - 5440 (2017)
We describe our efforts to improve the pharmacokinetic properties of a mechanism-based suicide inhibitor of the polyamine biosynthetic enzyme S-adenosylmethionine decarboxylase (AdoMetDC), essential for the survival of the eukaryotic parasite Trypanosoma brucei responsible for Human African Trypanosomiasis (HAT). The lead compound, 5′-(((Z)-4-amino-2-butenyl)methylamino)-5′-deoxyadenosine (1, also known as MDL 73811, or AbeAdo), has curative efficacy at a low dosage in a hemolymphatic model of HAT but displayed no demonstrable effect in a mouse model of the CNS stage of HAT due to poor blood–brain barrier permeation. Therefore, we prepared and evaluated an extensive set of analogs with modifications in the aminobutenyl side chain, the 5′-amine, the ribose, and the purine fragments. Although we gained valuable structure–activity insights from this comprehensive dataset, we did not gain traction on improving the prospects for CNS penetration while retaining the potent antiparasitic activity and metabolic stability of the lead compound 1.
An improved procedure for the synthesis of 1,3-dideazaadenosine
Devlin,Jebaratnam
, p. 711 - 718 (1995)
The preparation of the titled compound has been conveniently achieved in five steps, and in 43% overall yield. The large scale monoreduction of 2,6-dinitroaniline, and the stannic chloride catalyzed glycosylation of 4 to obtain 6 as the only product (86%) are two important reactions in this five step synthesis.
SUBSTITUTED BENZIMIDAZOLE CARBOXAMIDES AND THEIR USE IN THE TREATMENT OF MEDICAL DISORDERS
-
Paragraph 00297; 00309-00310; 0074, (2021/04/01)
The invention provides substituted benzimidazole carboxamides and related compounds, compositions containing such compounds, medical kits, and methods for using such compounds and compositions to treat a medical disorder, e.g., cancer, lysosomal storage disorder, neurodegenerative disorder, inflammatory disorder, in a patient.
Microwave use of amidine compounds in the aqueous phase benzoate synthesis of benzimidazole compounds method
-
Paragraph 0095, (2019/03/28)
The invention discloses a microwave the use of amidine compounds in the aqueous phase benzoate synthesis of benzimidazole compounds, in the aqueous phase under microwave conditions adding benzoic amidine compound under alkaline condition [...] into benzimidazole reaction, invention an environment-friendly, the operation is simple, cheap and safe, efficient process for preparing benzimidazole method. Compared with the prior art, this method not only can be applied to a large number of functional groups, the productive rate is high, few by-products, and the operation is simple, safe, low cost, environmental protection; .
Cu@U-g-C3N4 Catalyzed Cyclization of o-Phenylenediamines for the Synthesis of Benzimidazoles by Using CO2 and Dimethylamine Borane as a Hydrogen Source
Phatake, Vishal V.,Bhanage, Bhalchandra M.
, p. 347 - 359 (2018/11/23)
Abstract: This work reports a green and sustainable route for the synthesis of benzimidazoles via C–N bond formation using carbon dioxide (CO2) as a C1 carbon source. In this work, Cu@U-g-C3N4 catalyst was prepared from urea derived porous graphitic carbon?nitride (U-g-C3N4) and CuCl2 and characterized by FT-IR, XRD, XPS, SEM, TPD etc. The Cu@U-g-C3N4 as a heterogeneous recyclable catalyst has been employed first time for the cyclization of o-phenylenediamines (OPD) with CO2 to benzimidazoles using dimethylamine borane (DMAB). The proposed protocol becomes sustainable and efficient due to the use of propylene carbonate/water as a suitable biodegradable, economical and environmentally benign solvent system. The proposed catalytic system showed a wide range of substrate scope for the synthesis of benzimidazoles in good to excellent yields. Graphical Abstract: [Figure not available: see fulltext.]
Atom-Specific Mutagenesis Reveals Structural and Catalytic Roles for an Active-Site Adenosine and Hydrated Mg2+ in Pistol Ribozymes
Neuner, Sandro,Falschlunger, Christoph,Fuchs, Elisabeth,Himmelstoss, Maximilian,Ren, Aiming,Patel, Dinshaw J.,Micura, Ronald
supporting information, p. 15954 - 15958 (2017/11/21)
The pistol RNA motif represents a new class of self-cleaving ribozymes of yet unknown biological function. Our recent crystal structure of a pre-catalytic state of this RNA shows guanosine G40 and adenosine A32 close to the G53–U54 cleavage site. While the N1 of G40 is within 3.4 ? of the modeled G53 2′-OH group that attacks the scissile phosphate, thus suggesting a direct role in general acid–base catalysis, the function of A32 is less clear. We present evidence from atom-specific mutagenesis that neither the N1 nor N3 base positions of A32 are involved in catalysis. By contrast, the ribose 2′-OH of A32 seems crucial for the proper positioning of G40 through a H-bond network that involves G42 as a bridging unit between A32 and G40. We also found that disruption of the inner-sphere coordination of the active-site Mg2+ cation to N7 of G33 makes the ribozyme drastically slower. A mechanistic proposal is suggested, with A32 playing a structural role and hydrated Mg2+ playing a catalytic role in cleavage.
THERAPEUTICALLY ACTIVE COMPOUNDS AND THEIR METHODS OF USE
-
Page/Page column, (2015/02/19)
Provided are methods of treating a cancer characterized by the presence of a mutant allele of IDH1/2 comprising administering to a subject in need thereof a compound described here.
