Stereoselective synthesis and antimicrobial activity of benzofuran-based (1E)-1-(piperidin-1-yl)-N2-arylamidrazones

被引：76

作者：

Abdel-Aziz, Hatem A. ^{[1
]}

Mekawey, Amal A. I. ^{[2
]}

机构：

[1] Natl Res Ctr, Appl Organ Chem Dept, Cairo 12622, Egypt

[2] Al Azhar Univ, Reg Ctr Mycol & Biotechnol, Cairo, Egypt

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2009年 / 44卷 / 12期

关键词：

Benzofurans; Propanehydrazonoyl chlorides; Amidrazones; Sterioselectivity; X-ray crystallography; Antimicrobial activity; ANTIMYCOBACTERIAL ACTIVITY; N-MYRISTOYLTRANSFERASE; ANTIFUNGAL ACTIVITIES; ARYLHYDRAZONIC ACIDS; CONVENIENT SYNTHESIS; CRYSTAL-STRUCTURES; PART; DERIVATIVES; AMIDRAZONES; INHIBITORS;

D O I：

10.1016/j.ejmech.2009.09.002

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The reaction of 2-oxo-N-arylpropanehydrazonoyl chlorides 3a-e with 3-methyl-2-benzofurancarboxylic acid hydrazide (7) furnished N-(aryl)propanehydrazonoyl chlorides 8a-e. X-Ray of 8c revealed the (1Z,2E) configuration of structure 8. Nucleophilic substitution reaction of 8a or 8d with piperidine resulted in the formation of 1-(piperidin-1-yl)-N-2-arylamidrazones 9a, b. The X-ray diffraction of 9b showed its (I E,2E) configuration and it confirmed the stereoselectivity of the latter reaction. (1E,2Z,3E)-1 -(Piperidin-1-yl)-1-(arylhydrazono)-2-[(3-methylbenzofuran-2-oyl)hydrazonol-4-arylbut-3-enes 11 were synthesized in stereoselective reaction from 8 or alternatively from 9. X-ray analysis of 11b showed a conversion of configuration respect to 8d or 9b. X-Ray analysis of 9b, and 11b revealed the role of hydrogen interactions in the stereochemistry of their solid state structure. The in vitro antimicrobial activity of the newly synthesized compounds demonstrated an excellent growth inhibition of compounds 9 and 11 against clinically isolated strains of human fungal pathogens and exhibited a significant potency against Gram-positive bacteria. Griseofulvin and Amoxicilline were used as references for antifungal and antibacterial screening. The effect of most potent antifungal compound 9b on morphological features of Aspergillus fumigatus and Candida albicans using image analyzer was studied. Furthermore, the effect of 9b on the ultra-structures of the latter fungi was occurred by transmission electron microscope. (C) 2009 Elsevier Masson SAS. All rights reserved.

引用

页码：4985 / 4997

页数：13

共 53 条

[31] A new structural alternative in benzo[b]furans for antimicrobial activity [J].

Khan, MW ;

Alam, MJ ;

Rashid, MA ;

Chowdhury, R .

BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (16) :4796-4805

[32] Synthesis and antimicrobial activity of some novel derivatives of benzofuran: Part 2. The synthesis and antimicrobial activity of some novel 1-(1-benzofuran-2-yl)-2-mesitylethanone derivatives [J].

Kirilmis, Cumhur ;

Ahmedzade, Misir ;

Servi, Sueleyman ;

Koca, Murat ;

Kizirgil, Ahmet ;

Kazaz, Cavit .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2008, 43 (02) :300-308

[33] Synthesis and antimicrobial activity of some novel derivatives of benzofuran:: part 1.: Synthesis and antimicrobial activity of (benzofuran-2-yl)(3-phenyl-3-methylcyclobutyl) ketoxime derivatives [J].

Koca, M ;

Servi, S ;

Kirilmis, C ;

Ahmedzade, M ;

Kazaz, C ;

Özbek, B ;

Ötük, G .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2005, 40 (12) :1351-1358

[34] Novel benzofuran inhibitors of human mitogen-activated protein kinase phosphatase-1 [J].

Lazo, John S. ;

Nunes, Ruth ;

Skoko, John J. ;

de Oliveira, Pierre E. Queiroz ;

Vogt, Andreas ;

Wipf, Peter .

BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (16) :5643-5650

[35] Synthesis and Crystal Structure of a Compound with Two Conformational Isomers: N-(2-methylbenzoyl)-N′-(4-nitrophenyl)thiourea [J].

Li, Qian-Jin ;

Yang, Chun-Long .

JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, 2008, 38 (12) :927-930

[36] Synthesis and antimycobacterial activity of some N1-[1-[3-aryl-1-(pyridin-2-, 3-, or 4-yl)-3-oxo]propyl]-2-pyridinecarboxamidrazones [J].

Mamolo, MG ;

Falagiani, V ;

Vio, L ;

Banfi, E .

FARMACO, 1999, 54 (11-12) :761-767

[37] Microwave assisted synthesis of new indophenazine 1,3,5-trisubstruted pyrazoline derivatives of benzofuran and their antimicrobial activity [J].

Manna, Kuntal ;

Agrawal, Yadvendra K. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (10) :2688-2692

[38] Synthesis and biological activities of benzofuran antifungal agents targeting fungal N-myristoyltransferase [J].

Masubuchi, M ;

Ebiike, H ;

Kawasaki, E ;

Sogabe, S ;

Morikami, K ;

Shiratori, Y ;

Tsujii, S ;

Fujii, T ;

Sakata, K ;

Hayase, M ;

Shindoh, H ;

Aoki, Y ;

Ohtsuka, T ;

Shimma, N .

BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (20) :4463-4478

[39] Intermolecular CH•••N/CH•••O hydrogen bonds in the crystal structures of α,β-unsaturated ketones carrying a terminal pyridine subunit [J].

Mazik, M ;

Bläser, D ;

Boese, R .

TETRAHEDRON, 2001, 57 (27) :5791-5797

[40]

PAKS RMA, 1993, HDB MICROBIOL MEDIA, P278

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