Synthesis and evaluation of in vitro anti-microbial and anti-tubercular activity of 2-styryl benzimidazoles

Shingalapur, Ramya V.; Hosamani, Kallappa M.; Keri, Rangappa S.

doi:10.1016/j.ejmech.2009.05.021

Cited by 167 publications

(111 citation statements)

References 30 publications

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“…Particularily intriguing are quinoline and its derivatives as these have already found application as anticancer [3], antiviral [4] and antimalarial [5] agents. In view of the biological importance as well as possible pharmacological applications, the title compound was synthesized to study its crystal structure.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of ethyl 6-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate, C13H13NO3

Garudachari

Islor

Satyanarayan

et al. 2013

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of material amino]methylidene}propanedioate (1.0 g, 0.003 mol) and Dowtherm (10 mL) were heated to 250°C for 5 h. The reaction mixture was then cooled to 25°C and stirred in n-hexane (10 mL) for 10 min. The solid product obtained was filtered, dried and recrystallized from ethanol. Single crystals suitable for the X-ray diffraction study were grown by slow evaporation of a diluted ethanol solution of the compound at room temperature, yield: 0.79 g (95.1 %) [8]. DiscussionHeterocyclic derivatives attract the interest of medicinal chemists because of their varied biological activities such as their anti-microbial [1] or analgesic [2] properties. Particularily intriguing are quinoline and its derivatives as these have already found application as anticancer [3], antiviral [4] and antimalarial [5] agents. In view of the biological importance as well as possible pharmacological applications, the title compound was synthesized to study its crystal structure. Although the title compound could be present in an aromatic form spanning the whole core of the molecule (i.e. as ethyl 4-hydroxy-6-methylquinoline-3-carboxylate), a tautomer featuring only an aromatic system on the non-heterocyclic ring is observed in the solid state. The least-squares planes defined by the respective intracyclic atoms of each of the two sixmembered rings enclose an angle of just 1.41(11)°. The leastsquares plane defined by all non-hydrogen atoms of the aza-naphthalene core is essentially flat (r.m.s. of all fitted atoms = 0.015 Å) with the carbon atom bearing the ester substituent deviating most from the plane (by 0.026(2) Å). The hydrogen atom of the secondary amine group forms a hydrogen bond to the two doublebonded oxygen atom of the ester group. In terms of graph-set analysis [6,7], the descriptor for the N-H···O type hydrogen bond necessitates a C

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Section: Discussionmentioning

confidence: 99%

Crystal structure of ethyl 6-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate, C13H13NO3

Garudachari

Islor

Satyanarayan

et al. 2013

Zeitschrift Für Kristallographie - New Crystal Structures

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“…Imidazole is a structural unit of constructive histidine, histamine, and it is a part of purines which are molecules showing important biological functions in the human body. Some of the imidazole derivatives possess anti-inflammatory, antituberculotic, antimicrobial, antimycotic, antiviral and even antitumor activity [1][2][3][4][5][6][7]. Tinidazole, ornidazole and metronidazole are known as antimicrobials and antiparasites since the mid-1960s [8].…”

Section: Introductionmentioning

confidence: 99%

Spectroscopic (IR, Raman, UV–Vis) study and thermal analysis of 3d-metal complexes with 4-imidazolecarboxylic acid

Świderski

Wilczewska

Świsłocka

et al. 2018

J Therm Anal Calorim

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In this work, the spectroscopic (IR, Raman, UV-Vis) and thermal properties of 3d metal complexes with 4-imidazolecarboxylic acid were studied in order to determine the effect of 3d metals [i.e., Mn(II), Fe(III), Co(II), Ni(II), Cu(II), Zn(II)] on the electronic structure and physicochemical properties of the ligand. The spectroscopic studies showed that the 3d-transition metals stabilize the electronic system of 4-imidazolecarboxylic acid. Similar results were obtained previously for benzoic and pyridinecarboxylic acids. The complexes synthesized in an aqueous medium were hydrated, as determined by the elemental and thermogravimetric analysis. The complexes of 4-imidazolecarboxylic acid have the general formula: M(C 3 N 2 H 3 COO) x ÁnH 2 O where M = Mn, Fe, Co, Ni, Cu, Zn, x = 3 for iron complex, x = 2 for other complex and n = 0-3. Thermogravimetric analysis conducted in oxygen atmosphere showed that the complexes decompose to metal oxides. During the thermal decomposition process carbon monoxide, carbon dioxide and imidazole ring degradation products are released.

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“…Benzimidazole is an important pharmacophore and ap rivileged structure in medicinal chemistry encompassing adiverse range of biological activities [1]. Series of DNA-interactive benzimidazole analogues, such as Hoechst 33258 [2], were also prepared to explore the potential for anticancer activity mediated for certain of drugs via bio-reductive activation by endogenous nicotinamide adenine dinucleotide or nicotinamide adenine dinucleotide 2'-phosphate reduced tetrasodium salt [3].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of 2-(2-amino-5-chlorophenyl)-1H-benzimidazole, C13H10ClN3

Wang¹,

Li²,

Lin³

et al. 2010

Zeitschrift Für Kristallographie - New Crystal Structures

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Synthesis and evaluation of in vitro anti-microbial and anti-tubercular activity of 2-styryl benzimidazoles

Cited by 167 publications

References 30 publications

Crystal structure of ethyl 6-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate, C13H13NO3

Crystal structure of ethyl 6-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate, C13H13NO3

Spectroscopic (IR, Raman, UV–Vis) study and thermal analysis of 3d-metal complexes with 4-imidazolecarboxylic acid

Crystal structure of 2-(2-amino-5-chlorophenyl)-1H-benzimidazole, C13H10ClN3

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