Search for the pharmacophore in prazosin for Transport-P

Zunszain, Patricia A.; Cesare, Federico; Sechi, Mario; Al-Damluji, Saad; Ganellin, C. Robin

doi:10.1016/j.bmc.2005.03.030

Cited by 22 publications

(8 citation statements)

References 19 publications

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“…The intermediate 1 was obtained from commercially available 1,3-benzodioxole via five steps consisting of chloromethylation, 30) cyanation of chlorine atom, 31) hydrolysis of cyano group, 29,31) reduction of carboxyl group, 32) and bromination of hydroxyl group. 32,33) Compound 1 reacted with paraformaldehyde in concentrated hydrochloric acid containing small amount of POCl 3 at room temperature for 4-5 h to afford 2 in 95% yield. Compounds 3-n (n=1, 2 ··· 26) were formed via a bis-Sn2 cyclization of 2 with aniline or substituted anilines in aqueous solution of NaHCO 3 containing a small amount of sodium dodecyl sulfate (SDS) as phase transfer catalyst.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and <i>in Vitro</i> Antifungal Activities of New 2-Aryl-6,7-methylenedioxy-3,4-dihydroisoquinolin-2-ium Bromides

Yang

Yao

Qin

et al. 2013

CHEMICAL & PHARMACEUTICAL BULLETIN

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2-Aryl-3,4-dihydroisoquinolin-2-iums might be considered as a class of simple analogues of natural quaternary benzo[c]phenanthridine alkaloids. In this paper, 26 new 2-aryl-6,7-methylenedioxy-3,4-dihydroisoquinolin-2-ium bromides with various substituents in N-aromatic ring were synthesized from commercially available 1,3-benzodioxole in good to excellent yields. All the compounds were elucidated by MS, high resolution (HR)-MS, IR, 1 H-and 13 C-NMR analysis, and evaluated for antifungal activities in vitro against Alternaria alternate, Curvularia lunata and Fusarium oxysporum sp. niveum at 50 µg/mL. Most of the compounds showed higher activities against all the test fungi than their natural model compounds sanguinarine and chelerythrine. For A. alternate and Curvularia lunata, most of them were also more active than thiabendazole, a commercial fungicide standard. The structure-activity relationship indicated that the substituent in N-aromatic ring and its position had significant effect on the activity. The general trend was that halogen atoms and CF 3 remarkably enhanced the activity while CH 3 and OCH 3 decreased the activity. Generally, osubstituted isomers were more active than m-and p-substituted isomer. The present results suggest that the title compounds are potential for the development of new isoquinoline antimicrobial agents.Key words 3,4-dihydroisoquinolinium; 1,2,3,4-tetrahydroisoquinoline; N-heterocyclization; antifungal activity; CuCl 2 -catalyzed oxidative coupling reaction; 2,3-dichloro-5,6-dicyano-1,4-benzoquinone oxidation Alkaloids represent a very extensive group of secondary metabolites with diverse structures, distribution in nature, and biological effects. Natural isoquinolines are one of the largest groups of alkaloids. Among them, there is a relatively small but important class of iminium moiety-containing isoquinoline alkaloids, such as quaternary benzo[c] phenanthridine alkaloids (QBAs), quaternary N-naphthyl isoquinolines, berberines and so on 1,2) (Fig. 1). In the past decades, these compounds have aroused interests of both chemists and pharmacologists for their chemical reactivity and extensive bioactivities including antitumor, [3][4][5] antimicrobial, [6][7][8][9][10][11][12] anti-inflammation, 13) antiplatelet aggregation, 14) anti-angiogenesis, 15) anti-acetylcholinesterase, 16) and antiparasite activities. [17][18][19][20] Our previous studies demonstrated that sanguinarine and chelerythrine ( Fig. 1) might serve as ideal lead compounds to develop new isoquinoline antimicrobial and acaricidal agents. Meanwhile, the iminium moiety (C= N + ) was their determinant for their bioactivities. 11,12,17) The similar cases were also found for antitumor activity of 7-demethyl chelerythrine (NK109) 21) and antibacterial activity of berberine.9) In addition, the molecular planarity was also proven to be an important factor for the activity.21) Based on understanding of the structure-activity relationship above and the aim of developing more potent QBAs-like drugs, we intended to design a cl...

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Section: Resultsmentioning

confidence: 99%

Synthesis and <i>in Vitro</i> Antifungal Activities of New 2-Aryl-6,7-methylenedioxy-3,4-dihydroisoquinolin-2-ium Bromides

Yang

Yao

Qin

et al. 2013

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…For the agricultural and pharmaceutical relevance of 2-chloropyrimidin-4-amine, see: Zunszain et al (2005). For graph-set analysis of hydrogen bonds, see: Etter et al (1990); Bernstein et al (1995).…”

Section: Related Literaturementioning

confidence: 99%

“…The molecule of 2-chloropyrimidin-4-amine is relevant for agrochemistry as a plant growth regulator and as a pharmaceutical intermediate (Zunszain et al 2005). It could also be an interesting precursor for chelating ligands after chlorine substitution.…”

Section: Commentmentioning

confidence: 99%

2-Chloropyrimidin-4-amine

et al. 2012

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In the title pyrimidine derivative, C4H4ClN3, the 2-chloro and 4-amino substituents almost lie in the mean plane of the pyrimidine ring, with deviations of 0.003 (1) Å for the Cl atom, and 0.020 (1) Å for the N atom. In the crystal, molecules are linked via pairs of N—H⋯N hydrogen bonds, forming inversion dimers. These dimers are further linked via N—H⋯N hydrogen bonds, forming an undulating two-dimensional network lying parallel to (100).

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“…b) as a potent orally available ligand of the growth hormone secretagogue . On the other hand, heterocycles present in widely used losartan and valsartan are known with angiotensin receptor blocker properties (Fig. b).…”

Section: Introductionmentioning

confidence: 99%

Expedient Access to Novel Bis‐tetrazolopiperazines via Ugi‐azide Reactions

Ghandi

Sherafat

2016

Journal of Heterocyclic Chem

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A one‐pot four‐component synthesis of bis‐tetrazolopiperazines in moderate to high yields is described. The reaction consists of condensation of aldehydes or cyclic ketones with piperazine, trimethylsilyl azide, and isocyanides. High reaction efficiency, short reaction time, mild reaction condition, use of simple experimental procedure, and prompt isolation of the products are some advantages of this protocol.

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Search for the pharmacophore in prazosin for Transport-P

Cited by 22 publications

References 19 publications

Synthesis and <i>in Vitro</i> Antifungal Activities of New 2-Aryl-6,7-methylenedioxy-3,4-dihydroisoquinolin-2-ium Bromides

Synthesis and <i>in Vitro</i> Antifungal Activities of New 2-Aryl-6,7-methylenedioxy-3,4-dihydroisoquinolin-2-ium Bromides

2-Chloropyrimidin-4-amine

Expedient Access to Novel Bis‐tetrazolopiperazines via Ugi‐azide Reactions

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