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European Journal of Medicinal Chemistry 71 (2014) iii–xii
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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 GittoA 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.
NNN 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 MiyoshiDesign, 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 MizukamiixContents / 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 GhoshSubstituted 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. Meeganx 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 markerspp. 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 ParkA 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.
NO
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