European Journal of Medicinal Chemistry 71 (2014) iii–xii

Contents lists available at ScienceDirect

European Journal of Medicinal Chemistry

journal homepage: ht tp: / /www.elsevier .com/locate /e jmech

European Journal of Medicinal Chemistry Vol 71, 2014

Contents

ORIGINAL ARTICLES

Novel 2-chloro-4-anilino-quinazoline derivatives as EGFR and VEGFR-2 dual inhibitors

pp. 1–14 Maria Letícia de Castro Barbosa, Lídia Moreira Lima, Roberta Tesch, Carlos Mauricio R. Sant’Anna, Frank Totzke, Michael H.G. Kubbutat,Christoph Schächtele, Stefan A. Laufer and Eliezer J. Barreiro*

Importance of hydrophobic parameters in identifying appropriate pose of CYP substrates in cytochromes pp. 15–23

M. Ramesh and Prasad V. Bharatam*

The active site of cytochromes contains three regions: base, wall and dome. The wallregion is hydrophobic; thus, molecular docking imposing hydrophobic constraintleads to success in SOM prediction.

Design, synthesis and biological evaluation of imine resveratrol derivatives as multi-targeted agents againstAlzheimer’s disease

pp. 36–45

Su-Yi Li, Xiao-Bing Wang and Ling-Yi Kong*

A series of imine resveratrol derivatives were designed, synthesized, and evaluated asmulti-targeted compounds for the treatment of AD. 9 might be a promising compound forfurther study.

iv Contents / European Journal of Medicinal Chemistry 71 (2014) iii–xii

Synthesis of 3-heteryl substituted pyrrolidine-2,5-diones via catalytic Michael reaction and evaluationof their inhibitory activity against InhA and Mycobacterium tuberculosis

pp. 46–52

Tetiana Matviiuk, Giorgia Mori, Christian Lherbet*, Frédéric Rodriguez, Maria Rosalia Pasca, Marian Gorichko, Brigitte Guidetti,Zoia Voitenko** and Michel Baltas*

Synthesis and biological evaluation of new epalrestat analogues as aldose reductase inhibitors (ARIs) pp. 53–66

Thatikonda Narendar Reddy, Mettu Ravinder, Pankaj Bagul, Keerthi Ravikanti, Chandrakant Bagul, Jagadeesh Babu Nanubolu**,Kolupula Srinivas**, Sanjay K. Banerjee** and Vaidya Jayathirtha Rao*

Modifications/substitutions prevail: Four series of epalrestat analogues synthesized involving three structuralmodifications. In vitro aldose reductase activity and docking data generated for the epalrestat analogues informs thatfive compounds are potent.

Functionalized curcumin analogs as potent modulators of the Wnt/b-catenin signaling pathway

pp. 67–80 Pay-Chin Leow, Priti Bahety, Choon Pei Boon, Chong Yew Lee, Kheng Lin Tan, Tianming Yang and Pui-Lai Rachel Ee*

Exploring naphthyl-carbohydrazides as inhibitors of influenza A viruses

pp. 81–90 Sanmitra Barman, Lei You, Ran Chen, Vlad Codrea, Grace Kago, Ramakrishna Edupuganti, Jon Robertus, Robert M. Krug** andEric V. Anslyn*

vContents / European Journal of Medicinal Chemistry 71 (2014) iii–xii

Studies on the synthetic and structural aspects of benzosuberones bearing 2, 4-thiazolidenone moiety as potentialanti-cancer agents

pp. 91–97

Lingaiah Nagarapu*, Bandi Yadagiri, Rajashaker Bantu, C. Ganesh Kumar, Sujitha Pombala and Jagadesh Nanubolu

Cl

SNH

O

O

R

R

8a-b

Cl

SN

O

O O

R

R

R1

Head group Tail group

Thiazolidine core

6a-j

Synthesis and analysis of activity of a potential anti-melanoma prodrug with a hydrazine linker

pp. 98–104 Bo _zena Frackowiak-Wojtasek, Beata Gasowska-Bajger, Magdalena Mazurek, Agnieszka Raniszewska,Marieke Logghe, Ryszard Smolarczyk, Tomasz Cicho�n, Stanis1aw Szala and Hubert Wojtasek*

NCl

Cl

N

ON

H

H

OH

NCl

Cl

O

NN

OH OH

tyrosinase

Structure-based screening for the discovery of new carbonic anhydrase VII inhibitors

pp. 105–111 Laura De Luca*, Stefania Ferro, Francesca M. Damiano, Claudiu T. Supuran, Daniela Vullo, Alba Chimirri and Rosaria Gitto

A merged structure-based pharmacophore model has been generated thatled to the discovery of highly potent new carbonic anhydrase VII inhibitors.

Synthesis, biological activity and structure–activity relationships of new benzoic acid-based protein tyrosinephosphatase inhibitors endowed with insulinomimetic effects in mouse C2C12 skeletal muscle cells

pp. 112–127

Rosaria Ottanà, Rosanna Maccari*, Jérémie Mortier, Anna Caselli, Simona Amuso,Guido Camici, Archimede Rotondo, Gerhard Wolber and Paolo Paoli

vi Contents / European Journal of Medicinal Chemistry 71 (2014) iii–xii

Carbonic anhydrase inhibitors. Synthesis, and molecular structure of novel series N-substitutedN0-(2-arylmethylthio-4-chloro-5-methylbenzenesulfonyl)guanidines and their inhibition of human cytosolic isozymesI and II and the transmembrane tumor-associated isozymes IX and XII

pp. 135–147

Beata _Zo1nowska, Jaros1aw S1awi�nski*, Aneta Pogorzelska, Jaros1aw Chojnacki, Daniela Vullo and Claudiu T. Supuran

A series of novel N-substituted N0-(2-arylmethylthio-4-chloro-5-methylbenzenesulfonyl)guanidineshave been synthesized. Some of them exhibited a powerful carbonic anhydrase CAI, CAII, CAIX and CAXIIinhibitory potency as well as anticancer activity.

Synthesis and biological evaluation of a-triazolyl chalcones as a new type of potential antimicrobial agents and theirinteraction with calf thymus DNA and human serum albumin

pp. 148–159

Ben-Tao Yin, Cong-Yan Yan, Xin-Mei Peng, Shao-Lin Zhang, Syed Rasheed, Rong-Xia Geng* and Cheng-He Zhou*

A series of a-triazolyl chalcones were synthesized andscreened for their antimicrobial activities, further bindingbehavior with calf thymus DNA and human serum albuminwas investigated.

N

F

ON NN

MIC = 4 /mLAgainst MRSA and M. luteus

9a

300 400 500 600

0.0

0.5

1.0

1.5

Abs

orba

nce

Wavelength (nm)

a

k

DNA+NR

1 2 3 4

2

4

6

8

10

10-5 [Q]-1 (L/mol)

F0/

F0-

F

T = 286 KT = 298 KT = 310 K

Rational design and synthesis of novel dibenzo[b,d]furan-1,2,3-triazole conjugates as potent inhibitors ofMycobacterium tuberculosis

pp. 160–167

Thirumal Yempala, Jonnalagadda Padma Sridevi, Perumal Yogeeswari, Dharmarajan Sriram and Srinivas Kantevari*

2-(1H-Pyrazol-1-yl)acetic acids as chemoattractant receptor-homologous molecule expressed on Th2 lymphocytes(CRTh2) antagonists

pp. 168–184

Miriam Andrés, Mónica Bravo, Maria Antonia Buil, Marta Calbet, Marcos Castillo, Jordi Castro, Peter Eichhorn,Manel Ferrer, Martin D. Lehner, Imma Moreno, Richard S. Roberts* and Sara Sevilla

viiContents / European Journal of Medicinal Chemistry 71 (2014) iii–xii

1,2,4-Triazole/oxime hybrids as new strategy for nitric oxide donors: Synthesis, anti-inflammatory, ulceroginicity andantiproliferative activities

pp. 185–198

Gamal El-Din A.A. Abuo-Rahma, Mohamed Abdel-Aziz*, Eman A.M. Beshr and Taha F.S. Ali

Novel 1,2,4-triazole/oxime hybrids as new strategy for nitric oxide donors.

NN

N S

H

N

H CO

H CO

O

N

CH

NN

N S

H

N

H CO

H CO

O

N

CH

7k7cOH OH

Design, synthesis, molecular docking and 3D-QSAR studies of potent inhibitors of enoyl-acyl carrier protein reductaseas potential antimycobacterial agents

pp. 199–218

Uttam A. More, Shrinivas D. Joshi*, Tejraj M. Aminabhavi, Andanappa K. Gadad, Mallikarjuna N. Nadagouda and Venkatrao H. Kulkarni

Molecular docking and 3D-QSAR studies were done on pyrrole hydrazone derivatives as enoyl-ACP reductaseinhibitors in Mycobacterium tuberculosis.

Synthesis and tumor cell growth inhibitory activity of biotinylated annonaceous acetogenins

pp. 219–228 Jing-Fang Shi, Ping Wu, Zi-Hua Jiang** and Xiao-Yi Wei*

Synthesis and biological evaluation of a series of aminoalkyl-tetralones and tetralols as dual dopamine/serotoninligands

pp. 237–249

Laura Carro, María Torrado, Enrique Raviña, Christian F. Masaguer*, Sonia Lage, José Brea and María I. Loza

OH2N N

N O

F

36: 5-HT2A Ki = 5 nMD2 Ki = 47 nM

viii Contents / European Journal of Medicinal Chemistry 71 (2014) iii–xii

Discovery of a benzimidazole series of ADAMTS-5 (aggrecanase-2) inhibitors by scaffold hopping

pp. 250–258 Shinya Sogame, Yoshihito Suenaga, Masakazu Atobe*, Masashi Kawanishi, Eiichi Tanaka and Shiro Miyoshi

Design, synthesis, and biological evaluation of novel piperidine-4-carboxamide derivatives as potent CCR5 inhibitors

pp. 259–266 Suwen Hu, Quan Gu, Zhilong Wang, Zhiyong Weng, Yunrui Cai, Xiaowu Dong, Yongzhou Hu, Tao Liu* and Xin Xie**

16g and 16i showed equivalent inhibitory activity to that of the positive controlmaraviroc.

5

N

O

N

O

N

N

Cl

ON

O

N

O

NN

ClO

N

O

N

O

NN

ClO

n

RR

Group-reverseStrategy

Anilides and quinolones with nitrogen-bearing substituents from benzothiophene and thienothiophene series:Synthesis, photochemical synthesis, cytostatic evaluation, 3D-derived QSAR analysis and DNA-binding properties

pp. 267–281

Maja Aleksi�c, Branimir Berto�sa**, Raja Nhili, Sabine Depauw, Irena Martin-Kleiner, Marie-Hélène David-Cordonnier, Sanja Tomi�c,Marijeta Kralj and Grace Karminski-Zamola*

CH3)2N(CH2)3ClxHClNaH/DMF

CH3INaH/DMF

HCl(g)/EtOH

or

S

NH

R

O

3a, 3b, 8a, 8b, 11, 12

S

N

R

O

R'

9a, 9b, 10, 13, 14, 15

A novel tamoxifen derivative, ridaifen-F, is a nonpeptidic small-molecule proteasome inhibitor

pp. 290–305 Makoto Hasegawa*, Yukari Yasuda, Makoto Tanaka, Kenya Nakata, Eri Umeda, Yanwen Wang, Chihiro Watanabe, Shoko Uetake,Tatsuki Kunoh, Masafumi Shionyu, Ryuzo Sasaki, Isamu Shiina** and Tamio Mizukami

ixContents / European Journal of Medicinal Chemistry 71 (2014) iii–xii

Synthesis of novel pyrano[3,2-f]quinoline, phenanthroline derivatives and studies of their interactions with proteins: pp. 306–315

An application in mammalian cell imaging K.C. Majumdar*, Sudipta Ponra, Tapas Ghosh, Ratan Sadhukhan and Utpal Ghosh

Substituted quinoline derivatives have been synthesized by a simple and inexpensiveHCl-mediated 6-‘endo-trig’ Michael type ring closure. The synthesized quinolinesexhibit staining property and can be used as fluorophores.

Synthesis and biological evaluation of novel substituted 1,3,4-thiadiazole and 2,6-di aryl substituted imidazo [2,1-b][1,3,4] thiadiazole derivatives

pp. 316–323

B. Chandrakantha, Arun M. Isloor*, Prakash Shetty, Hoong Kun Fun and Gurumurthy Hegde

The manuscript deals with the synthesis of new series of 1,3,4-thiadiazole 4(a–l) and 2,6-di aryl imidazo [2,1-b] [1,3,4] thiadiazole 6 (a–l) derivatives.Synthesized compounds were characterized and screened for their anti-microbial activities.

R

NO2

S

NN

NH

O

4(a-l)R

S

NN

N

NO2

O

6(a-l)

Synthesis and evaluation of 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(4-(2-(4-substitutedpiperazin-1-yl)acetyl)piperazin-1-yl)quinoline-3-carboxylic acid derivatives as anti-tubercular and antibacterial agents

pp. 324–332

Narva Suresh, Hunsur Nagendra Nagesh, Janupally Renuka, Vikrant Rajput, Rashmi Sharma, Inshad Ali Khan and Chandra SekharKondapalli Venkata Gowri*

Synthesis and antiproliferative action of a novel series of maprotiline analogues

pp. 333–353 Y.M. McNamara, S.A. Bright*, A.J. Byrne, S.M. Cloonan, T. McCabe, D.C. Williams and M.J. Meegan

x Contents / European Journal of Medicinal Chemistry 71 (2014) iii–xii

Synthesis and characterization of new N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)amide/sulfonamidederivatives as possible antimicrobial and antitubercular agents

pp. 354–365

Pakkath Karuvalam Ranjith, Rajeesh Pakkath, Karickal R. Haridas* and Suchetha N. Kumari

Synthesis, characterization and SAR studies of a new series of N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)amide and N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl) sulfonamide derivativesand their antimicrobial, antitubercular studies.

N

N

Cl

O

HN R

O

N

N

Cl

O

HNS

O

R

O

Region 2

Region 1

Platinated benzonaphthyridone is a stronger inhibitor of poly(ADP-ribose) polymerase-1 and a more potent pp. 366–373

anticancer agent than is the parent inhibitor Beilei Wang, Hui Qian, Shek-Man Yiu, Jianwei Sun and Guangyu Zhu*

99m

Development and biological evaluation of Tc-sulfonamide derivatives for in vivo visualization of CA IX as surrogatetumor hypoxia markers

pp. 374–384

Vamsidhar Akurathi, Ludwig Dubois, Sofie Celen, Natasja G. Lieuwes, Satish K. Chitneni,Bernard J. Cleynhens, Alessio Innocenti, Claudiu T. Supuran, Alfons M. Verbruggen, Philippe Lambin and Guy M. Bormans*

SHORT COMMUNICATIONS

Access to a new class of biologically active quinoline based 1,2,4-triazoles

pp. 24–30 Rahul V. Patel* and Se Won Park

A new class of quinoline based 1,2,4-triazoles has been equipped withpotent antifungal efficacy. Effect of substitution pattern of different phar-macophore in the designed scaffold system on antimicrobial activity iselaborated.

xiContents / European Journal of Medicinal Chemistry 71 (2014) iii–xii

Antimicrobial activity of de novo designed cationic peptides against multi-resistant clinical isolates

pp. 31–35 Diego Faccone, Omar Veliz, Alejandra Corso, Martin Noguera, Melina Martínez, Cristian Payes, Liliana Semorile and Paulo Cesar Maffía*

De novo designed alpha helical cationic peptides with antimicrobial activity against multi-resistant clinical isolates.

Urea/oxalamide tethered b-lactam-7-chloroquinoline conjugates: Synthesis and in vitro antimalarial evaluation

pp. 128–134 Pardeep Singh, Raghu Raj, Parvesh Singh, Jiri Gut, Philip J. Rosenthal and Vipan Kumar*

Synthesis and in vitro antimalarial evaluation of urea and oxalamide tethered b-lactam-7-chloroquinoline conjugates.

N

O

NH

R

OC2H5

ON

O

NH

RO

N

HN NH2

Cl

OC2H5

O

n

NCl

HN NH

O HN

O NO R

n

NCl

HN NH

NH

O

n

NO R

Synthesis, characterization and anticancer screening of some novel piperonyl–tetrazole derivatives

pp. 229–236 Mohammad Arshad, Abdul Roouf Bhat, Smritee Pokharel, Ji-Eun Kim, Eun Ju Lee, Fareeda Athar* and Inho Choi**

1,2-Substitued tetrazole derivatives were synthesized and screened in ERpositive and negative Breast cancer cell lines. Derivatives which showed 10–30 percent negative growth were studied unto marker gene expression.

Synthesis and evaluation of the antiparasitic activity of bis-(arylmethylidene) cycloalkanones

pp. 282–289 Saulo F.P. Braga, Érika V.P. Alves, Rafaela S. Ferreira, Jordana R.B. Fradico, Paula S. Lage, Mariana C. Duarte, Tatiana G. Ribeiro, Policarpo A.S.Júnior, Alvaro J. Romanha, Maiko L. Tonini, Mário Steindel, Eduardo F. Coelho and Renata B. de Oliveira*

xii Contents / European Journal of Medicinal Chemistry 71 (2014) iii–xii

COVER

This picture is taken from the article published in: European Journal of Medicinal Chemistry, 2013 Volume 68, Pages 1–9. Synthesis, biological evaluation andmolecular docking studies of pyrazole derivatives coupling with a thiourea moiety as novel CDKs inhibitors 2013 Published by Elsevier Masson SAS

* Corresponding authors.

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Cited/Abstracted in : Biological Abstracts, Chemical Abstracts, CABS, CNRS/Pascal, Current Contents (Life Sciences), EMbase, Index Medicus/Medline, Science CitationIndex. Also covered in the abstract and citation database SCOPUS�. Full text available on ScienceDirect�.

ISSN 0223-5234