Synthesis and antiviral activity of fluorinated pyrido[1,2-a]benzimidazoles

Kotovskaya, S. K.; Baskakova, Z. M.; Charushin, Valery N.; Чупахин, О. Н.; Belanov, E. F.; Бормотов, Н. И.; Balakhnin, S. M.; Серова, О. А.

doi:10.1007/s11094-006-0023-9

Cited by 88 publications

(38 citation statements)

References 9 publications

(8 reference statements)

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“…Among them, Imidazo[1,2‐ a ]pyridine is the most important in the area of pharmaceuticals and natural products. These heterocyclic derivatives like imidazopyridine and imidazopyrimidines show a wide range of biological activities like anti‐inflammatory, antiviral, antimicrobacterial, antitumor antifungal and anticancer …”

Section: Introductionmentioning

confidence: 99%

Design and Synthesis of Piperazine‐Linked Imidazo[1,2‐a]pyridine Derivatives as Potent Anticancer Agents

et al. 2019

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Designed, synthesized a series of novel imidazo[1,2-a]pyridine derivatives and evaluated for their in vitro cytotoxicity. Fluorine containing compounds, (2-fluorophenyl)(4-(2-(pyridin-2-yl)imidazo[1,2-a]pyridin-6-yl)piperazin-1-yl)methanone (7 e),(4-(2-(pyridin-2-yl)imidazo[1,2-a]pyridin-6-yl)piperazin-1-yl)(2-(trifluoromethyl)phenyl)methanone (7 h) and (3-fluorophenyl) (4-(2-(pyridin-2-yl)imidazo[1,2-a]pyridin-6-yl)piperazin-1-yl)methanone (7 i) were found to have an effective cytotoxic profile against HepG2, HeLa and MDA-MB-231. Compounds 7 h (IC 50 = 5.8 μM) and 7 i (IC 50 = 3.5 μM) were found potent when compared with control Paclitaxel (IC 50 = 2.8 μM), against HeLa. Compound 7 h also found to be potent against HepG2 (IC 50 = 2.0 μM) and MDAMB-231(IC 50 = 6.9 μM) respectively, when compared with Paclitaxel (HepG2, IC 50 = 0.56 μM; MDAMB-231, IC 50 = 1.9 μM). Compound 7 e also found to be potent against HepG2 (IC 50 = 9.8 μM) cell lines. Synthesized piperazine linked imidazo[1,2-a]pyridine derivatives (7 i, IC 50 = 3.5 μM) and (7 h, IC 50 = 5.8 μM) showed 1.74 fold, 1.12 fold increase in antiproliferative activity than reported homopiperazine linked imidazo [1,2-a]pyrimidine derivatives (4-Fluorophenyl)(4-(2-(4fluorophenyl)imidazo[1,2-a]pyrimidin-7-yl)-1,4-diazepan-1-yl)methanone(10 f, IC 50 = 6.12 μM) and (4-(2-(4-Fluorophenyl)imidazo[1,2-a]pyrimidin-7-yl)-1,4-diazepan-1-yl)(3methoxyphenyl)methanone (12, IC 50 = 6.54 μM) against Hela cell lines. Molecular docking studies showed that designed compounds occupy at the active site of both colchicine and human estrogen receptor which demonstrated that the designed compounds were able to bind with multiple targets, the biological activity of these compounds hold promise to find application in considering for treatment protocol.[a] M.

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Section: Introductionmentioning

confidence: 99%

Design and Synthesis of Piperazine‐Linked Imidazo[1,2‐a]pyridine Derivatives as Potent Anticancer Agents

et al. 2019

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“…Some alkylsilyl substituted benzimidazole derivatives have also been reported to possess important antitumor activity 28, 29. Since benzimidazole compounds have been found to have a broad range of pharmacological activity, many research groups as well as our group have been interested in these types of heterocyclic compounds 30–40…”

Section: Introductionmentioning

confidence: 99%

Synthesis, microwave-promoted catalytic activity in Suzuki-Miyaura cross-coupling reactions and antimicrobial properties of novel benzimidazole salts bearing trimethylsilyl group

Yılmaz

Küçükbay

Şırecı

et al. 2011

Appl. Organometal. Chem.

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A mixture of benzimidazole salts (2-7), Pd(OAc) 2 and K 2 CO 3 in DMF-H 2 O catalyzes the Suzuki-Miyaura cross-coupling reactions promoted by microwave irradiation resulting in high yield within a short time. In particular, the yield of the Suzuki-Miyaura reactions with aryl bromides was found to be nearly quantitative. The synthesized benzimidazole salts (2-7) were identified by 1 H-13 C, NMR, IR spectroscopic methods and microanalysis. The molecular structure of 1 was determined by X-ray crystallography. The antibacterial and antifungal activities of the novel benzimidazole derivatives (1-7) were also tested against standard strains.

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“…This interest is related to the close analogy between the electronic characteristics of such fluoroarenes and hydroxypyrimidines (e.g., between 2,4-difluorotoluene and thymine) and to the ability of fluoroarenes to coordination with heterocyclic bases of nucleic acids [6]. In continuation of our previous investigations into the synthesis of fluorine-containing azaheterocycles [7,8], we have developed methods for the preparation of fluorinated 3-phenyl-1,2,4-benzotriazines (see scheme below), obtained a series of compounds of this type, and studied their antiviral activity.…”

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confidence: 88%

Synthesis and antiviral activity of fluorinated 3-phenyl-1,2,4-benzotriazines

Kotovskaya¹,

Zhumabaeva²,

Perova³

et al. 2007

Pharm Chem J

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New synthetic approaches to fluorinated 3-phenyl-1,2,4-benzotriazines for biological testing have been elaborated. 1-(3,4-Difluorophenyl)-3,5-diphenylformazan (IVa) was synthesized via dinitriding of 3,4-difluoroaniline, followed by azo-addition of the resulting azobenzenediazonium chloride with acetaldehyde phenylhydrazone. 6,7-Difluoro-3-phenyl-1,2,4-benzotriazine (Va) was obtained via intramolecular cyclization of formazan IVa in the presence of BF3/AcOH complex. Monofluoro-substituted 6-R-7-fluoro-3-phenyl-1,2,4-benzotriazine derivatives (Vb -Vq) were prepared by substituting fluorine atom with alkoxides in 3,4-difluoronitrobenzene. Conditions for nucleophilic substitution of the second fluorine atom in benzotriazines V have been established. Fluorinated 3-phenyl-1,2,4-benzotriazines have been tested for antiviral and cytotoxic activity on Vero cell cultures and proved to be active against severe diseases caused by smallpox and some other pathogenic viruses.

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Synthesis and antiviral activity of fluorinated pyrido[1,2-a]benzimidazoles

Cited by 88 publications

References 9 publications

Design and Synthesis of Piperazine‐Linked Imidazo[1,2‐a]pyridine Derivatives as Potent Anticancer Agents

Design and Synthesis of Piperazine‐Linked Imidazo[1,2‐a]pyridine Derivatives as Potent Anticancer Agents

Synthesis, microwave-promoted catalytic activity in Suzuki-Miyaura cross-coupling reactions and antimicrobial properties of novel benzimidazole salts bearing trimethylsilyl group

Synthesis and antiviral activity of fluorinated 3-phenyl-1,2,4-benzotriazines

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