Quinazoline and benzimidazole MCH-1R antagonists

Arienzo, Rosa; Cramp, Sue; Dyke, Hazel J.; Lockey, Peter; Norman, Dennis; Roach, A. G.; Smith, Phil; Wong, Melanie; Wren, Stephen P.

doi:10.1016/j.bmcl.2006.11.092

Cited by 19 publications

(6 citation statements)

References 10 publications

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“…For background to benzoheterocyclic derivatives and their applications, see: Arienzo et al (2007); Chassaing et al (2008); Galarcei et al (2008); Kumar & Rajput (2009); Kung et al (2009); Podunavac-Kuzmanovic & Cvetkovic (2010); Via et al (2001); Xue et al (2011); Zhang et al (2009). For related structures, see: Eltayeb et al (2007Eltayeb et al ( , 2009Eltayeb et al ( , 2011a.…”

Section: Related Literaturementioning

confidence: 99%

“…Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009). Benzoheterocyclic derivatives have been used widely in the pharmaceutical industry and medicine due to their diverse pharmaceutical activities (Arienzo et al, 2007;Chassaing et al, 2008;Kumar et al, 2009;Kung et al, 2009;Podunavac-Kuzmanovic & Cvetkovic, 2010;Zhang et al, 2009) including inhibition against enteroviruses (Xue et al, 2011) and potent antitumor activity (Galarcei et al, 2008;Via et al, 2001). Due to their interesting activities, the benzimidazole and quinazoline scaffolds were selected for our ongoing structural studies (Eltayeb et al, 2007;2009;2011a;2011b).…”

Section: Data Collectionmentioning

confidence: 99%

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2-(5,6-Dihydrobenzimidazo[1,2-c]quinazolin-6-yl)-5-methoxyphenol

et al. 2011

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In the title quinazoline derivative, C21H17N3O2, the benzimidazole unit makes dihedral angles of 8.29 (5) and 81.79 (5)° with the benzene rings of the quinazoline and methoxyphenol units, respectively. The nitrogen-containing six-membered ring adopts a half-chair conformation. In the crystal, the molecules are linked through O—H⋯N hydrogen bonds into screw chains along the b axis; adjacent chains are further connected by N—H⋯O hydrogen bonds, thereby forming a two-dimensional network lying parallel to the bc plane. Weak C—H⋯π and π⋯π interactions with centroid–centroid distances of 3.5258 (8) and 3.7184 (7) Å are present and N⋯O [2.6816 (15) and 3.0519 (15) Å] short contacts also occur.

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Section: Related Literaturementioning

confidence: 99%

Section: Data Collectionmentioning

confidence: 99%

2-(5,6-Dihydrobenzimidazo[1,2-c]quinazolin-6-yl)-5-methoxyphenol

et al. 2011

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“…Quinazolinone ligands have a diverse range of pharmacological properties [1][2][3][4] and applications in several areas such as electronics, anti-corrosive agents, polymers, optical materials and fluorescent tags in DNA sequencing [5][6][7]. Recently, quinazolin-4(3H)-ones and condensed quinazolin-4(3H)-ones have been found to possess potent central nervous system activities including analgesic, anti-inflammatory and anti-convulsant effects [8][9][10].…”

Section: Introductionmentioning

confidence: 99%

Manganese(II), cobalt(II) and nickel(II) complexes with 2-phenyl-3-(benzylamino)-1,2-dihydroquinazolin-4(3H)-one, pseudohalides and some bidentate N-donor ligands

Sawant

Yamgar

Chavan

2010

Transition Met Chem

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Some mixed ligand complexes of the type [M(L) (en or phen)(X) 2 ]; where M = Mn(II), Co(II) or Ni(II); L = 2-phenyl-3-(benzylamino)-1,2-dihydroquinazolin-4(3H)-one; en = ethylenediamine, phen = 1,10-phenanthroline; X = N 3 -or NCS -have been prepared. All the complexes were characterized by physico-chemical, spectroscopic and thermal studies. On the basis of electronic spectra and magnetic susceptibility measurements, an octahedral geometry has been proposed for all the complexes. The phen complexes are thermally more stable than the en complexes. The electrochemical behavior of the Ni(II) complexes showed that the complexes of phen are reduced at more positive potential compared to the corresponding en complexes.

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“…It is present in many compounds like Vit B 12 , albendazole, mebendazole and thiabendazole which are used as antihelmintic drugs 12,13 . The 2-substituted benzimidazoles and their derivatives have been found to possess various biological activities including as inhibitors of MDA-MB-231 human breast cancer cell proliferation 14 , TRPV1 antagonists 15 , selective antagonists of the human melanocortin-4 receptor 16 , kinase inhibitors 17 , antimicrobial activity 18 and MCH-1R antagonists 19 . Benzothiophene analogues represent major class of medicinally important compound and possess wide variety of activities including vascular 5-HT 1B receptor 20 , selective inhibitors of IKK-ε kinase 21 , partial agonist activity at the benzodiazepine receptor 22 , ligands for α 1 -and 5HT 1A -receptors 23 .…”

Section: Introductionmentioning

confidence: 99%

Microwave Assisted Liquid Phase Synthesis of Benzimidazolo Benzothiophenes for Antimicrobial Activity

Kini¹,

Kumar²,

Ghate³

2009

Journal of Chemistry

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Benzimidazolo benzothiophene derivatives were prepared by liquid phase combinatorial synthesis using soluble polymer support PEG 5000 and 4-fluoro-3-nitrobenzoic acid as starting materials with substituted primary amines. All these synthesized compounds were established by the spectral data and tested for antimicrobial activity against gram positive bacteria, i.e. S. aureus, B. subtilis and gram negative bacteria, E.coli and P.aeruginosa and anti fungal activity against C. albicans. Ampicillin and ciprofloxacin were used as standard for antibacterial activity and cotrimoxazole for anti fungal activity. Compared with standards compounds (1a-h) showed significant activity against bacterial species and 1g showed significant activity against fungal species.

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Quinazoline and benzimidazole MCH-1R antagonists

Cited by 19 publications

References 10 publications

2-(5,6-Dihydrobenzimidazo[1,2-c]quinazolin-6-yl)-5-methoxyphenol

2-(5,6-Dihydrobenzimidazo[1,2-c]quinazolin-6-yl)-5-methoxyphenol

Manganese(II), cobalt(II) and nickel(II) complexes with 2-phenyl-3-(benzylamino)-1,2-dihydroquinazolin-4(3H)-one, pseudohalides and some bidentate N-donor ligands

Microwave Assisted Liquid Phase Synthesis of Benzimidazolo Benzothiophenes for Antimicrobial Activity

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