Recurrence of the oxazole motif in tubulin colchicine site inhibitors with anti-tumor activity

被引:21
作者
Barreca, Marilia [1 ]
Spano, Virginia [1 ]
Raimondi, Maria Valeria [1 ]
Tarantelli, Chiara [2 ,3 ]
Spriano, Filippo [2 ,3 ]
Bertoni, Francesco [2 ,3 ]
Barraja, Paola [1 ]
Montalbano, Alessandra [1 ]
机构
[1] Univ Palermo, Dept Biol Chem & Pharmaceut Sci & Technol STEBICEF, Via Archirafi 32, I-90123 Palermo, Italy
[2] USI, Fac Biomed Sci, Inst Oncol Res, Via Vincenzo Vela 6, CH-6500 Bellinzona, Switzerland
[3] Oncol Inst Southern Switzerland, Via Osped, CH-6500 Bellinzona, Switzerland
来源
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY REPORTS | 2021年 / 1卷
关键词
Oxazoles; Anti-Tubulin agents; Cancer; Colchicine binding inhibitors; BIOLOGICAL EVALUATION; COMBRETASTATIN A-4; ANTIPROLIFERATIVE ACTIVITY; BRIDGED ANALOGS; TUMOR-GROWTH; DERIVATIVES; ISOXAZOLE; NVP-AUY922; BEARING; DESIGN;
D O I
10.1016/j.ejmcr.2021.100004
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Because of its wide spectrum of targets and biological activities, the oxazole ring is a valuable heterocyclic scaffold in the design of new therapeutic agents with anticancer, antiviral, antibacterial, anti-inflammatory, neuroprotective, antidiabetic and antidepressant properties. The presence of two heteroatoms, oxygen and nitrogen, offers possible interactions (hydrogen, hydrophobic, van der Waals or dipoles bonds) with a broad range of receptors and enzymes. Furthermore, the oxazole core conjugates low cytotoxicity with improved compound solubility and is well suited to structural modifications such as substitution with different groups and condensation to aromatic, heteroaromatic or non-aromatic rings, offering diversity when introduced into scaffolds. These features make it a very attractive nucleus in medicinal chemistry. Herein we present a diverse array of oxazole derivatives with potential therapeutic use in multiple tumor models. The emphasis has been addressed to compounds with anti-tubulin activity reported in literature in the last decade, describing their structural features, efficiency and future perspectives.
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页数:9
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共 55 条
[21]   Discovery and SAR study of c-Met kinase inhibitors bearing an 3-amino-benzo[d] isoxazole or 3-aminoindazole scaffold [J].
Jiang, Xiaolong ;
Liu, Hongyan ;
Song, Zilan ;
Peng, Xia ;
Ji, Yinchun ;
Yao, Qizheng ;
Geng, Meiyu ;
Ai, Jing ;
Zhang, Ao .
BIOORGANIC & MEDICINAL CHEMISTRY, 2015, 23 (03) :564-578
[22]   Isoxazole-type derivatives related to combretastatin A-4, synthesis and biological evaluation [J].
Kaffy, Julia ;
Pontikis, Renee ;
Carrez, Daniele ;
Croisy, Alain ;
Monneret, Claude ;
Florent, Jean-Claude .
BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (12) :4067-4077
[23]   Synthesis and biological evaluation of 3,5-diaryl isoxazoline/isoxazole linked 2, 3-dihydroquinazolinone hybrids as anticancer agents [J].
Kamal, Ahmed ;
Bharathi, E. Vijaya ;
Reddy, J. Surendranadha ;
Ramaiah, M. Janaki ;
Dastagiri, D. ;
Reddy, M. Kashi ;
Viswanath, A. ;
Reddy, T. Lakshminarayan ;
Shaik, T. Basha ;
Pushpavalli, S. N. C. V. L. ;
Bhadra, Manika Pal .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (02) :691-703
[24]   Phase 1B/2 study of the HSP90 inhibitor AUY922 plus trastuzumab in metastatic HER2-positive breast cancer patients who have progressed on trastuzumab-based regimen [J].
Kong, Anthony ;
Rea, Daniel ;
Ahmed, Samreen ;
Beck, J. Thaddeus ;
Lopez, Rafael Lopez ;
Biganzoli, Laura ;
Armstrong, Anne C. ;
Aglietta, Massimo ;
Alba, Emilio ;
Campone, Mario ;
Schmitz, Shu-Fang Hsu ;
Lefebvre, Caroline ;
Akimov, Mikhail ;
Lee, Soo-Chin .
ONCOTARGET, 2016, 7 (25) :37680-37692
[25]   New Indole Tubulin Assembly Inhibitors Cause Stable Arrest of Mitotic Progression, Enhanced Stimulation of Natural Killer Cell Cytotoxic Activity, and Repression of Hedgehog-Dependent Cancer [J].
La Regina, Giuseppe ;
Bai, Ruoli ;
Coluccia, Antonio ;
Farniglini, Valeria ;
Pelliccia, Sveva ;
Passacantilli, Sara ;
Mazzoccoli, Carmela ;
Ruggieri, Vitalba ;
Verrico, Annalisa ;
Miele, Andrea ;
Monti, Ludovica ;
Nalli, Marianna ;
Alfonsi, Romina ;
Di Marcotullio, Lucia ;
Gulino, Alberto ;
Ricci, Biancamaria ;
Soriani, Alessandra ;
Santoni, Angela ;
Caraglia, Michele ;
Porto, Stefania ;
Da Pozzo, Eleonora ;
Martini, Claudia ;
Brancale, Andrea ;
Marinelli, Luciana ;
Novellino, Ettore ;
Vultaggio, Stefania ;
Varasi, Mario ;
Mercurio, Ciro ;
Bigogno, Chiara ;
Dondio, Giulio ;
Hamel, Ernest ;
Lavia, Patrizia ;
Silvestri, Romano .
JOURNAL OF MEDICINAL CHEMISTRY, 2015, 58 (15) :5789-5807
[26]   Identification of CKD-516: A Potent Tubulin Polymerization Inhibitor with Marked Antitumor Activity against Murine and Human Solid Tumors [J].
Lee, Jaekwang ;
Kim, Soo Jin ;
Choi, Hojin ;
Kim, Young Hoon ;
Lim, In Tack ;
Yang, Hyun-mo ;
Lee, Chang Sik ;
Kang, Hee Ryong ;
Ahn, Soon Kil ;
Moon, Seung Kee ;
Kim, Dal-Hyun ;
Lee, Sungsook ;
Choi, Nam Song ;
Lee, Kyung Joo .
JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (17) :6337-6354
[27]   Bioactive pyrrole-based compounds with target selectivity [J].
Li Petri, Giovanna ;
Spano, Virginia ;
Spatola, Roberto ;
Holl, Ralph ;
Raimondi, Maria Valeria ;
Barraja, Paola ;
Montalbano, Alessandra .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2020, 208
[28]   Synthesis and biological evaluation of 3,4-diaryl-5-aminoisoxazole derivatives [J].
Liu, Tao ;
Dong, Xiaowu ;
Xue, Na ;
Wu, Rui ;
He, Qiaojun ;
Yang, Bo ;
Hu, Yongzhou .
BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (17) :6279-6285
[29]   Methods in Tubulin Proteomics [J].
Miller, Leah M. ;
Xiao, Hui ;
Burd, Berta ;
Horwitz, Susan Band ;
Angeletti, Ruth Hogue ;
Verdier-Pinard, Pascal .
MICROTUBULES, IN VITRO: MICROTUBULES, IN VITRO, 2010, 95 :105-126
[30]   Synthesis and anti-tumor activity of novel combretastatins: Combretocyclopentenones and related analogues [J].
Nam, NH ;
Kim, Y ;
You, YJ ;
Hong, DH ;
Kim, HM ;
Ahn, BZ .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (15) :1955-1958