Abstract
A number of N-substituted 2-amino-5-(2,4-dihydroxyphenyl)-1,3,4-thiadiazoles were synthesized and evaluated for their antiproliferative activities. The panel substitution included alkyl, aryl, and morpholinoalkyl derivatives. The structures of compounds were identified from elemental, IR, (1)H NMR, (13)C NMR and MS spectra analyses. The cytotoxicity in vitro against the four human cell lines: SW707 (rectal), HCV29T (bladder), A549 (lung), and T47D (breast) was determined. Alkyl and morpholinoalkyl derivatives exhibited significantly lower effect than phenyl ones. The highest antiproliferative activity was found for 2-(2,4-dichlorophenylamino)-5-(2,4-dihydroxyphenyl)-1,3,4-thiadiazole, with ID(50) two times lower (SW707, T47D) than for cisplatin studied comparatively as the control compound.
References
Jul 4, 1990·Journal of the National Cancer Institute·P SkehanM R Boyd
Feb 1, 1990·American Journal of Clinical Oncology·R F AsburyR Mortel
Jan 1, 1986·Cancer Chemotherapy and Pharmacology·J A StewartI H Krakoff
Jun 1, 1988·Investigational New Drugs·P J ElsonT E Davis
Oct 1, 1987·American Journal of Clinical Oncology·R F AsburyD G Haller
Aug 1, 1986·American Journal of Clinical Oncology·R F AsburyP J DiSaia
Nov 1, 1985·Chemical & Pharmaceutical Bulletin·K MiyamotoK Takatori
Sep 1, 1995·Bioorganic & Medicinal Chemistry·L MishraK Takeya
Aug 1, 1996·American Journal of Clinical Oncology·R AsburyD Moore
Jun 20, 2000·European Journal of Medicinal Chemistry·J MatysiakT Kornillowicz
Oct 18, 2000·European Journal of Pharmaceutical Sciences : Official Journal of the European Federation for Pharmaceutical Sciences·A MastrolorenzoC T Supuran
Apr 20, 2001·Bioorganic & Medicinal Chemistry·C T SupuranA Scozzafava
Nov 21, 2001·Journal of Agricultural and Food Chemistry·J MatysiakA Niewiadomy
Aug 8, 2002·Il Farmaco·S Karakuş, S Rollas
Apr 26, 2003·Bioorganic & Medicinal Chemistry·Joanna Matysiak, Andrzej Niewiadomy
Jun 24, 2003·Biochemical Pharmacology·Jui-Yi ChouJih-Hwa Guh
Mar 1, 1956·Proceedings of the Society for Experimental Biology and Medicine·I H KRAKOFF, G B MAGILL
Jun 1, 1959·The Journal of Clinical Investigation·I H KRAKOFF, M E BALIS
Mar 1, 1964·Biochemical Pharmacology·I H KRAKOFF
Mar 12, 2004·Anti-cancer Drugs·Andrea Senff-RibeiroMaria B M Oliveira
Dec 24, 2004·Journal of Medicinal Chemistry·Elçin E OruçAnatholy S Dimoglo
Citations
Nov 15, 2011·Archives of Pharmacal Research·Monika M KarpińkaAndrzej Niewiadomy
Jan 22, 2013·European Journal of Medicinal Chemistry·Asif HusainRavinesh Mishra
Feb 26, 2013·European Journal of Medicinal Chemistry·Navin B PatelGildardo Rivera
Feb 5, 2013·European Journal of Medicinal Chemistry·Alicja SkrzypekPaweł Szymański
May 31, 2011·Nucleosides, Nucleotides & Nucleic Acids·Rong WanQiu He
Jul 15, 2011·Acta Crystallographica. Section E, Structure Reports Online·Jin-Hua YaoJian-Ning Guan
Nov 8, 2011·Acta Crystallographica. Section E, Structure Reports Online·S MohanM N Ponnuswamy
Jun 1, 2013·Acta Crystallographica. Section E, Structure Reports Online·H D KavithaH C Devarajegowda
Jul 5, 2006·Chemical & Pharmaceutical Bulletin·Joanna Matysiak
Mar 21, 2015·Journal of Enzyme Inhibition and Medicinal Chemistry·Tomasz PlechPiotr Paneth
Mar 5, 2013·Chemical Biology & Drug Design·Abhishek Kumar JainRam Kishore Agrawal
Jan 1, 2013·International Journal of Medicinal Chemistry·Bhawna SharmaUpendra Kumar Sharma
Jul 28, 2012·Biochimica Et Biophysica Acta·Daniel M KamińskiMariusz Gagoś
Mar 14, 2007·Bioorganic & Medicinal Chemistry·Wojciech RzeskiMartyna Kandefer-Szerszeń
Jan 17, 2015·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Sobhi M GomhaAbdou O Abdelhamid
Dec 5, 2012·ChemMedChem·Yijing LiGuisen Zhao
Oct 15, 2013·Archiv der Pharmazie·Leila HosseinzadehAlireza Aliabadi
Apr 24, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Georgeta Serban
Apr 10, 2020·Anti-cancer Agents in Medicinal Chemistry·Malavattu G PrasadManojit Pal
Feb 4, 2011·Archiv der Pharmazie·Joanna MatysiakIzabela Dybała
Jul 4, 2018·Molecular Diversity·Maria ShafiqueNajim Aboud Al-Masoudi
May 8, 2015·Chemical & Pharmaceutical Bulletin·Nadia Youssef Megally Abdo, Mona Monir Kamel
Jun 30, 2014·Molecular Diversity·Peng LiuRun-Tao Li
Jul 22, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Abdou O AbdelhamidSaher M Kandeel
Nov 1, 2017·Chemistry Central Journal·Sobhi M GomhaAhmad M Alhajoj
Sep 17, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Grzegorz CzernelArkadiusz Matwijczuk
Apr 23, 2015·Bioorganicheskaia khimiia·E Jagiełło-WójtowiczK Sarna
Sep 4, 2020·Pharmacological Reports : PR·Monika Szeliga
Jan 28, 2020·Bioorganic Chemistry·Mohammad Rashid
Feb 20, 2020·Acta Pharmaceutica : a Quarterly Journal of Croatian Pharmaceutical Society and Slovenian Pharmaceutical Society, Dealing with All Branches of Pharmacy and Allied Sciences·Georgeta Serban
Apr 11, 2014·Chemical Reviews·Yang HuHai-Liang Zhu