4414-88-4Relevant articles and documents
Synthesis and antifungal activity of novel α-alkoxyimino-(1H-benzoimidazol-2-yl)acetonitriles containing piperazine moiety
Jin, Qingdong,Li, Fubo,Li, Ying,Jin, Fei,Jiang, Lin
, p. 7695 - 7702 (2015)
A series of α-alkoxyimino-[1-(4-methylpiperazino-1-yl)carbonylmethyl-1H-benzimidazol-2-yl] acetonitriles were synthesized from o-phenylenediamine, ethyl cyanoacetate, chloroacetyl piperazine, and haloalkane/benzyl chloride by multi-step reactions. The structures of the target compounds were elucidated by IR, 1H NMR, MS, and elemental analysis. All the target compounds were tested for in vitro antifungal activities against Sclerotinia sclerotiorum and Botrytis cinerea by the mycelium growth rate method, and the results indicated that some compounds displayed higher antifungal activity as compared to carbendazim.
MECHANISMS FOR THE SOLVOLYTIC DECOMPOSITIONS OF NUCLEOSIDE ANALOGUES-I. ACIDIC HYDROLYSIS OF 2-SUBSTITUTED 1-(1-ETHOXYETHYL)BENZIMIDAZOLES
Loennberg, Harri,Kaeppi, Rainer
, p. 913 - 918 (1980)
A few 2-substituted 1-(1-ethoxyethyl)benzimidazoles have been prepared and the rate constants for their hydrolysis measured at various temperatures and oxonium ion concentrations.The formal kinetics followed and the effect of varying the 2-substitution on the hydrolysis rate suggest that the acid-catalyzed cleavage of these compounds involves a rapid initial protonation of the benzimidazole ring and a subsequent rate-limiting heterolysis of the protonated substrate to form a free nitrogen base and an oxocarbenium ion derived from the ethoxyethyl group.The values obtained for the entropy of activation are consistent with the assumed u nimolecular nature of the rate-limiting step.The effects of 2-substituents on the acidities of the protonated substrates and their heterolysis rates have been compared.The latter partial reaction has been suggested to be the subject of steric acceleration.
Synthesis of novel thiophene, thiazole and coumarin derivatives based on benzimidazole nucleus and their cytotoxicity and toxicity evaluations
Mohareb, Rafat Milad,Abdallah, Amira Elsayed Mahmoud,Mohamed, Abeer Abdelazeem
, p. 309 - 318 (2018)
The reactivity of compounds 2-(1-(2-chloroacetyl)-1 H-benzo[d]imidazol-2-yl)acetonitrile 2 and 3-(1-(2-chloroacetyl)-1 H-benzo[d]imidazol-2-yl)-2H-chromen-2-one 8 towards different chemical reagents were studied and a series of novel benzimidazole derivatives were obtained (2-6a-d and 8-12a-d). Moreover, in vitro growth inhibitory effect of the newly synthesized compounds were evaluated in term of [IC50 μM] against the six cancer cell lines, human lung carcinoma (A549), lung cancer (H460), human colorectal (HT29), gasteric cancer cell (MKN-45), glioma cell line (U87MG) and cellosaurus cell line (SMMC-7721) where foretinib was used as standard reference. The results showed that compounds 2 (only for A549 cell line), 3a, 4, 6c, 6d, 8, 9a, 9e and 9f were the most active compounds towards the six cancer cell lines. On the other hand, the toxicity of these most potent compounds against shrimp larvae indicated that compounds 3a, 4, 6d, 9e and 9f were non toxic while compounds 6c and 8 were very toxic and compounds 2 and 9a were harmful against the tested organisms.
Synthesis and in vivo evaluation of novel benzimidazole-sulfonamide hybrids and Lucilia cuprina maggots' excretion/secretion topical gels for wound healing
Sayed, Asmaa M.,Saleh, Nashwa M.,El-Gaby, Mohamed S. A.,Abdel-Samad, Mohammad R. K.,Taher, Fatma A.
, p. 1291 - 1301 (2021/02/16)
A novel series of benzimidazole-sulfonamide hybrids (6a–g) was designed, synthesized, and their structures were characterized by 1H NMR and 13C NMR spectral data. Further, all compounds were evaluated for their antibacterial effects. The synthesized benzimidazole-sulfonamide hybrid (6d) showed the highest antibacterial activity against Staphylococcus aureus, Staphylococcus epidermis, Escherichia coli, and Klebsiella pneumonia. Different gel formulations for 6d were prepared and physically investigated. After in vivo evaluation for wound healing, the 6d gel formulation delayed the wound healing in animal model. But interestingly, a combination of 6d and Lucilia cuprina maggots' excretion/secretion showed remarkable enhancement in wound healing compared with 6d only. This combination opens up promising prospects for wound healing formulations.
Novel benzimidazole-acrylonitrile hybrids and their derivatives: Design, synthesis and antimycobacterial activity
Sirim, Mustafa Mert,Krishna, Vagolu Siva,Sriram, Dharmarajan,Unsal Tan, Oya
, (2019/12/30)
This paper reports the synthesis and evaluation of some benzimidazole-acrylonitrile hybrid derivatives for their in vitro antimycobacterial activities against Mycobacterium tuberculosis H37Rv. Among the derivatives studied, 3b was found to be the most active compound with MIC of 0.78 μg/mL against M. tuberculosis. This is a quite good activity compared with ethambutol (MIC = 1.56 μg/mL). Moreover, 3b showed 2.8 log fold reduction in bacterial count of dormant forms of mycobacterium which is more potent than first line drugs isoniazid, ciprofloxacin, rifampicin and moxifloxacin. Having activities against both active and dormant forms of M. tuberculosis, 3b may be a useful candidate for the development of new drugs to treat tuberculosis.
Plastic colorant fluorescent red GK and preparation method thereof
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Paragraph 0036-0038; 0042-0044; 0048-0050, (2020/12/30)
The invention belongs to the technical field of plastic colorants, and particularly relates to a plastic colorant fluorescent red GK and a preparation method thereof. The plastic colorant fluorescentred GK comprises the following raw materials in parts by weight: 37-39 parts of ethylene glycol monoethyl ether, 0.9 - 1.1 parts of malononitrile and 4.9- 5.1 parts of 3 -(1H-benzimidazole -2-yl)-N, N-diethyl -2-imine -2H-1-benzopyran- 7-amine. The preparation method of the plastic colorant fluorescent red GK comprises the following steps: 1) condensation: sequentially adding ethylene glycol monoethyl ether, malononitrile and 3- (1H-benzimidazole- 2-yl)-N, N-diethyl -2-imine -2H-1-benzopyran -7-amine in proportion into a condensation kettle, heating to 125-135 DEG C, reacting for 5.5-6.5 hours, cooling to 45-55 DEG C, discharging, and filtering to obtain a filter cake; and 2) filtering and drying: drying the filter cake in an environment with normal pressure and a temperature of 60-80 DEGC to prepare the plastic colorant fluorescent red GK. The preparation method of the plastic colorant fluorescent red has the characteristics of short reaction time, mild reaction conditions, low equipment requirements and high reaction yield.
Antimalarial Pyrido[1,2- a]benzimidazole Derivatives with Mannich Base Side Chains: Synthesis, Pharmacological Evaluation, and Reactive Metabolite Trapping Studies
Okombo, John,Brunschwig, Christel,Singh, Kawaljit,Dziwornu, Godwin Akpeko,Barnard, Linley,Njoroge, Mathew,Wittlin, Sergio,Chibale, Kelly
, p. 372 - 384 (2019/01/26)
A novel series of pyrido[1,2-a]benzimidazoles bearing Mannich base side chains and their metabolites were synthesized and evaluated for in vitro antiplasmodium activity, microsomal metabolic stability, reactive metabolite (RM) formation, and in vivo antimalarial efficacy in a mouse model. Oral administration of one of the derivatives at 4 × 50 mg/kg reduced parasitemia by 95% in Plasmodium berghei-infected mice, with a mean survival period of 16 days post-treatment. The in vivo efficacy of these derivatives is likely a consequence of their active metabolites, two of which showed potent in vitro antiplasmodium activity against chloroquine-sensitive and multidrug-resistant Plasmodium falciparum (P. falciparum) strains. Rapid metabolism was observed for all the analogues with 40% of parent compound remaining after 30 min of incubation in liver microsomes. RM trapping studies detected glutathione adducts only in derivatives bearing 4-aminophenol moiety, with fragmentation signatures showing that this conjugation occurred on the phenyl ring of the Mannich base side chain. As with amodiaquine (AQ), interchanging the positions of the 4-hydroxyl and Mannich base side group or substituting the 4-hydroxyl with fluorine appeared to block bioactivation of the AQ-like derivatives though at the expense of antiplasmodium activity, which was significantly lowered.
Regioselective transmonocyanoacetylation of o-phenylenediamine derivatives: simple and efficient synthesis of 2-cyanomethylbenzimidazole derivatives
Ammar, Yousry A.,Abbas, Samir Y.,Fouad, Sawsan A.,Salem, Mohamed A.,El-gaby, Mohamed S. A.
, p. 639 - 643 (2019/02/17)
A simple and efficient method for the regioselective transmonocyanoacetylation of o-phenylenediamine derivatives was developed using 1-cyanoacetyl-3,5-dimethylpyrazole as a cyanoacetylating agent. This method provided operationally simple and efficient access to a series of N-(2-aminophenyl)-2-cyanoacetamide derivatives under mild conditions with short reaction time. Also, 2-cyanomethylbenzimidazole derivatives have been synthesized through the cyclocondensation of N-(2-aminophenyl)-2-cyanoacetamide derivatives. In all cases, high yield of products was obtained and reaction times were significantly reduced with relation to similar reactions.
Antioxidative and antiproliferative activities of novel pyrido[1,2-a]benzimidazoles
Tireli, Martina,Star?evi?, Kristina,Martinovi?, Tamara,Paveli?, Sandra Kraljevi?,Karminski-Zamola, Grace,Hranjec, Marijana
, p. 201 - 210 (2017/02/15)
A series of pyrido[1,2-a]benzimidazoles has been designed, and novel examples are synthesized and evaluated for their potential antiproliferative activity against four human tumour cell lines—cervical (HeLa), colorectal (SW620), breast (MCF-7) and hepatocellular carcinoma (HepG2). In addition, their antioxidative potency has been evaluated by in vitro spectrophotometric assays. Preliminary structure–activity relationships among the synthesized compounds are discussed. Evaluation of their antioxidative capacity has shown that two compounds (25 and 26) possess promising reducing characteristics and free radical scavenging activity. Selective antiproliferative effect in the single-digit micromolar range was observed for compound 25 on MCF-7 (IC50=6μM) and HeLa (IC50=8μM) cell lines, comparable to the standards 5-fluorouracil and cisplatin. The combination of the radical scavenging activity and antiproliferative activity of compound 25 positions this compound as a potential lead candidate for further optimization.
Design, synthesis, docking and QSAR study of substituted benzimidazole linked oxadiazole as cytotoxic agents, EGFR and erbB2 receptor inhibitors
Akhtar, Md Jawaid,Siddiqui, Anees Ahmad,Khan, Ahsan Ahmed,Ali, Zulphikar,Dewangan, Rikeshwer Prasad,Pasha, Santosh,Yar, M. Shahar
, p. 853 - 869 (2016/12/22)
The synthesis of benzimidazole linked oxadiazole derivatives designed as potential EGFR and erbB2 receptor inhibitors with anticancer and apoptotic activity were studied. Compounds 7a specifically inhibit EGFR and erbB2 receptor at 0.081 and 0.098 μM concentration. Some of the compounds showed strong, broad-spectrum antiproliferative activitiy when tested against five human cancer cell lines. Compounds 7a and 7n were more cytotoxic than 5-fluorouracil against MCF-7 cancer cell, with IC50values of 5.0 and 2.55 μM whereas, only 7a led to cell cycle arrest at G2/M phase accompanied by an increase in apoptosis. Compounds 7a and 7n showed normal architecture of myofibrils in cardiomyopathy study whereas only compound 7a showed nearly equal biochemical parameters (SGOT and SGPT) when compared to control. Molecular docking & 3D-QSAR studies were used to establish interactions of 7a and 7n within the active site of enzyme for ATP binding site of kinase domain.
