Synthesis and biological activities of novel antiallergic agents with 5-lipoxygenase inhibiting action

Nakano, Hirofumi; Inoue, Tsutomu; Kawasaki, Nana; Miyataka, Hideki; Matsumoto, Hitoshi; Taguchi, Takeo; Inagaki, Nobuya; Nagai, Hiroichi; Satoh, Toshifumi

doi:10.1016/s0968-0896(99)00291-6

Cited by 209 publications

(120 citation statements)

References 20 publications

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“…This great attention is essentially due to their wide range of biopharmacological activities including antihelminthic [1], antitumoral [2], antimicrobial [3], antifungal [4], antiviral [5], antihistaminic and antiallergic [6] properties. The benzimidazole derivatives showed to be also excellent inhibitors of HIV-1 reverse transcriptase [7].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of 1-(1H-benzimidazol-2-yl)-3- (3-nitrophenyl)prop-2-en-1-one, C16H11N3O3

Bisseyou¹,

Guillot²,

Sissouma³

et al. 2011

Zeitschrift Für Kristallographie - New Crystal Structures

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C 16 H 11 N 3 O 3 ,monoclinic, P12 1 /c1(no. 14), a =9.3959(2) Å, b =5.7085(1) Å, c =24.8921(7) Å, b =96.885(1)°, V =1325.5 Å 3 , Z =4,Rgt(F) =0.041, wRref(F 2 ) =0.152, T =100 K.Source of material 2-Acetylbenzimidazole (1.5 g, 10 mmol) was dissolved to asolution of EtOH (40 ml) and 3g(75 mmol) of NaOH. To this solution, 10 mmol of 3-nitrobenzaldehyde was added. The mixture was stirred at ambient temperature during 5h.The resulting mixture was neutralized with a4Nsolution of HCl. The precipitate was dried and recrystallized from amixture of toluene/EtOH (4 : 1, v/v)(yield 68 %, m.p. >533 K). Yellow crystals of parallelepiped shape suitable for single-crystal diffraction were grown by slow evaporation at ambient temperature and in air from ahot solution in acetonitrile. NMR data are available in the CIF. Experimental details DiscussionBenzimidazole and its derivatives constitute one of the most extensively studied families of organic compounds in regard to the number of articles published on these compounds. This great attention is essentially due to their wide range of biopharmacological activities including antihelminthic [6] properties. The benzimidazole derivatives showed to be also excellent inhibitors of HIV-1 reverse transcriptase [7]. The benzimidazole nucleus system, whose inestimable virtues seduced the scientific community, was moreover classified as an important pharmacophore in the discovery of modern drug [8]. From this point of view, the benzimidazole nucleus system constitutes abasic molecular scaffold in the design of new molecules of pharmacological interest. The title molecular structure consists of three main parts: the benzimidazole ring and the nitrophenyl ring related by enone group (figure, top). In the benzimidazole ring the bond lengths and angles are in good agreement with those observed in the 1-(1H-benzimidazol-2-yl)-3-(3-chlorophenyl)-prop-2-en-1-one [9]. The C10=N2 double bond and C16-N2 single bond in the imidazole ring are clearly distinguishable with bond lengths of 1.323(2) and 1.387(1) Å,r espectively. The benzimidazole ring makes dihedral angles of 2.66(3)°and 1.16(3)°with phenyl ring and mean plane of enone group, respectively. It confers to the molecule an almost planar structure. The magnitudes of structural parameters of phenyl ring are within normal ranges [10], with a light opening of intramolecular angle at C4 atom due to the presence of nitro group which is twisted of 13°with respect of phenyl ring. The N3-O2 and N3-O3 bonds of nitro group have similar distances of 1.226 (2)

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Section: Discussionmentioning

confidence: 99%

Crystal structure of 1-(1H-benzimidazol-2-yl)-3- (3-nitrophenyl)prop-2-en-1-one, C16H11N3O3

Bisseyou¹,

Guillot²,

Sissouma³

et al. 2011

Zeitschrift Für Kristallographie - New Crystal Structures

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“…Benzimidazole is a potential heterocyclic pharmacophore responsible for a number of important pharmacological properties, such as anti-pyretic, antihistaminic, anti-allergic (Nakano et al, 2000), and anti-ulcerative (Scott et al, 2002). They are also effective against various viruses like influenza, human cyto-megalovirus, and HIV.…”

Section: 2-disubstituted Benzimidazolementioning

confidence: 99%

Recent Advances in Biomimetic Synthesis Involving Cyclodextrins

Nageswar¹,

Murthy²,

Madhav³

et al. 2011

Advances in Biomimetics

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“…The high therapeutic properties of the related drugs have encouraged the medicinal chemists to synthesize a large number of novel chemotherapeutic agents [10][11][12]. They displayed many biological activities, such as: antiviral [13] and antitumoral [14]; antifungal and antimycotic [15]; antihistaminic and antiallergic [16]; antimicrobial [17][18][19][20] and antihelminthic activity [21]; all are unique characteristics known for benzimidazole derivatives [10]. These compounds are also extensively used in industrial processes as corrosion inhibitors for metal and alloy surfaces [22,23].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Spectral and Theoretical Characterization of 5,6-Dichloro/Dimethyl-2-(2´,3´/2´,4´/2´,5´/3´,4´/3´,5´-Dimethoxyphenyl)-1H-Benzimidazoles

Gürbüz¹,

Tavman²,

Çınarli³

et al. 2016

ChemJMold

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Abstract. 5,6-Dichloro/dimethyl-2-(2´,3´/2´,4´/2´,5´/3´,4´/3´,5´-dimethoxyphenyl)-1H-benzimidazoles were synthesized and characterized by using analytical data, FT-IR, FT-Raman, NMR, ESI-MS and fl uorescence spectroscopy. The optimized molecular geometry, zero point energy, dipole moment, ESE, band gap and charge distributions were calculated by Gaussian 09 using Density Functional Theory (DFT, RB3LYP) with 6-31++G(d,p) basis set. According to the calculations, the molecules have structures with various torsion angles between the benzimidazole and benzene rings from 9.7º to 47.8º. The calculated energy values with ZPE correction and DFT show that the methyl derivatives are more stable than the chloro forms. 3´,4´-Dimethoxy derivatives have higher decomposition points in comparison with the other compounds in series. The chlorine atoms of 5,6-dichloro-2-(2´,3´/2´,4´/2´,5´/3´,4´/3´,5´-dimethoxyphenyl)-1H-benzimidazoles are positively charged whereas the C5 and C6 carbon atoms are negatively charged due to the attached chlorine atoms, in virtue of the electron withdrawing characteristic of the imidazole part of the benzimidazole ring. Also, some calculated prominent bond lengths and bond angles were discussed.

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Synthesis and biological activities of novel antiallergic agents with 5-lipoxygenase inhibiting action

Cited by 209 publications

References 20 publications

Crystal structure of 1-(1H-benzimidazol-2-yl)-3- (3-nitrophenyl)prop-2-en-1-one, C16H11N3O3

Crystal structure of 1-(1H-benzimidazol-2-yl)-3- (3-nitrophenyl)prop-2-en-1-one, C16H11N3O3

Recent Advances in Biomimetic Synthesis Involving Cyclodextrins

Synthesis, Spectral and Theoretical Characterization of 5,6-Dichloro/Dimethyl-2-(2´,3´/2´,4´/2´,5´/3´,4´/3´,5´-Dimethoxyphenyl)-1H-Benzimidazoles

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