Development of selective and reversible pyrazoline based MAO-A inhibitors: Synthesis, biological evaluation and docking studies

被引：53

作者：

Karuppasamy, Muthukumar ^{[1
]}

Mahapatra, Manojkumar ^{[1
]}

Yabanoglu, Samiye ^{[2
]}

Ucar, Gulberk ^{[2
]}

Sinha, Barij Nayan ^{[1
]}

Basu, Arijit ^{[1
]}

Mishra, Nibha ^{[1
]}

Sharon, Ashoke ^{[3
]}

Kulandaivelu, Umasankar ^{[4
]}

Jayaprakash, Venkatesan ^{[1
]}

机构：

[1] Birla Inst Technol, Dept Pharmaceut Sci, Ranchi 835215, Bihar, India

[2] Hacettepe Univ, Fac Pharm, Dept Biochem, TR-06100 Ankara, Turkey

[3] Birla Inst Technol, Dept Appl Chem, Ranchi 835215, Bihar, India

[4] Vaagdevi Coll Pharm, Med Chem Res Div, Warangal 506001, Andhra Pradesh, India

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2010年 / 18卷 / 05期

关键词：

Pyrazolines; MAO inhibitors; Molecular docking; BRAIN MONOAMINE-OXIDASE; 1-N-SUBSTITUTED THIOCARBAMOYL-3-PHENYL-5-THIENYL-2-PYRAZOLINES; ANTIDEPRESSANT ACTIVITIES; B INHIBITORS; DERIVATIVES; TRENDS;

D O I：

10.1016/j.bmc.2010.01.043

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

070307 [化学生物学]; 071010 [生物化学与分子生物学];

摘要：

3,5-Diaryl pyrazolines analogs were synthesized and evaluated for their monoamine oxidase (MAO) inhibitory activity. The compounds were found reversible and selective towards MAO-A with selectivity index in the magnitude of 10(3)-10(5). The docking studies were carried out to gain further structural insights of the binding mode and possible interactions with the active site of MAO-A. Interestingly, the theoretical (K-i) values obtained by molecular docking studies were in congruence with their experimental (K-i) values. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：1875 / 1881

页数：7

共 35 条

[1]

BILGIN AA, 1993, ARZNEIMITTEL-FORSCH, V43-2, P1041

[2]

Insights into the mode of inhibition of human mitochondrial monoamine oxidase B from high-resolution crystal structures [J].

Binda, C ;

Li, M ;

Hubálek, F ;

Restelli, N ;

Edmondson, DE ;

Mattevi, A .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2003, 100 (17) :9750-9755

[3]

BRADFORD MM, 1976, ANAL BIOCHEM, V72, P248, DOI 10.1016/0003-2697(76)90527-3

[4]

Carreiras MC, 2004, CURR PHARM DESIGN, V10, P3167

[5]

Synthesis, biological evaluation and 3D-QSAR of 1,3,5-trisubstituted-4,5-dihydro-(1H)-pyrazole derivatives as potent and highly selective monoamine oxidase a inhibitors [J].

Chimenti, F ;

Bolasco, A ;

Manna, F ;

Secci, D ;

Chimenti, P ;

Granese, A ;

Befani, O ;

Turini, P ;

Cirilli, R ;

La Torre, F ;

Alcaro, S ;

Ortuso, F ;

Langer, T .

CURRENT MEDICINAL CHEMISTRY, 2006, 13 (12) :1411-1428

[6]

Synthesis, molecular modeling studies, and selective inhibitory activity against monoamine oxidase of 1-thiocarbamoyl-3,5-diaryl-4,5-dihydro-(1H)-pyrazole derivatives [J].

Chimenti, F ;

Maccioni, E ;

Secci, D ;

Bolasco, A ;

Chimenti, P ;

Granese, A ;

Befani, O ;

Turini, P ;

Alcaro, S ;

Ortuso, F ;

Cirilli, R ;

La Torre, F ;

Cardia, MC ;

Distinto, S .

JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (23) :7113-7122

[7]

Synthesis and selective inhibitory activity of 1-acetyl-3,5-diphenyl-4,5-dihydro-(1H)-pyrazole derivatives against monoamine oxidase [J].

Chimenti, F ;

Bolasco, A ;

Manna, F ;

Secci, D ;

Chimenti, P ;

Befani, O ;

Turini, P ;

Giovannini, V ;

Mondovì, B ;

Cirilli, R ;

La Torre, F .

JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (08) :2071-2074

[8]

Three-dimensional structure of human monoamine oxidase A (MAO A): Relation to the structures of rat MAO A and human MAO B [J].

De Colibus, L ;

Li, M ;

Binda, C ;

Lustig, A ;

Edmondson, DE ;

Mattevi, A .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2005, 102 (36) :12684-12689

[9]

A new therapeutic approach in Alzheimer disease:: Some novel pyrazole derivatives as dual MAO-B inhibitors and antiinflammatory analgesics [J].

Goekhan-Kelekci, Nesrin ;

Yabanoglu, Samiye ;

Kuepeli, Esra ;

Salgin Goksen, Umut ;

Oezgen, Oezen ;

Ucar, Guelerk ;

Yesilada, Erdem ;

Kendi, Engin ;

Yesilada, Akguel ;

Bilgin, A. Altan .

BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (17) :5775-5786

[10]

1-N-substituted thiocarbamoyl-3-phenyl-5-thienyl-2-pyrazolines:: Synthesis and evaluation as MAO inhibitors [J].

Gökhan, N ;

Yesilada, A ;

Uçar, G ;

Erol, K ;

Bilgin, AA .

ARCHIV DER PHARMAZIE, 2003, 336 (08) :362-371

← 1 2 3 4 →