Green synthesis and biological evaluation of some new benzothiazolo [2,3-b] quinazolin-1-ones as anticancer agents
详细信息    查看全文
  • 作者:Jaiprakash N. Sangshetti ; Deepak K. Lokwani…
  • 关键词:Aminobenzthiazole ; Cyclic diketones ; Water ; mediated reaction ; Benzothiazoloquinazolinones ; Anticancer activity ; Docking study
  • 刊名:Medicinal Chemistry Research
  • 出版年:2014
  • 出版时间:November 2014
  • 年:2014
  • 卷:23
  • 期:11
  • 页码:4893-4900
  • 全文大小:798 KB
  • 参考文献:1. Abida OR, Khalida M, Hussainb MT, Hanif M, Qadeer G, Ramaa NH, Kornienkoc A, Khan KM (2012) Synthesis and anti-cancer, anti-metastatic evaluation of some new fluorinated isocoumarins and 3,4-dihydroisocoumarins. J Fluor Chem 135:240-45 CrossRef
    2. Alagarsamy V, Thangathiruppathy A, Mandal SC, Rajasekaran S, Vijaykumar S (2006) Pharmacological evaluation of 2-substituted (1,3,4) thiadiazolo quinazolines. Ind J Pharm Sci 68:108-11 CrossRef
    3. Brasca MG, Amboldi N, Ballinari D, Cameron A, Casale E, Cervi G, Colombo M, Colotta F, Croci V, D’Alessio R, Fiorentini F, Isacchi A, Mercurio C, Moretti W, Panzeri A, Pastori W, Pevarello P, Quartieri F, Roletto F, Traquandi G, Vianello P, Vulpetti A, Ciomei M (2009) Identification of / N,1,4,4-tetramethyl-8-{[4-(4-methylpiperazin-1-yl)phenyl]amino}-4,5-dihydro-1 / H-pyrazolo[4,3- / h]quinazoline-3-carboxamide (PHA-848125), a potent, orally available cyclin dependent kinase inhibitor. J Med Chem 52:5152-163 CrossRef
    4. Caputo R, Calabro ML, Micale N, Schimmer AD, Ali M, Zappala M, Grasso S (2012) Synthesis of benzothiazole derivatives and their biological evaluation as anticancer agents. Med Chem Res 21:2644-651 CrossRef
    5. Choi SJ, Lee JE, Jeong SY, Im I, Lee SD, Lee EJ, Lee SK, Kwon SM, Ahn SG, Yoon JH, Han SY, Kim JI, Kim YC (2010) 5,5-Substituted indirubin-3-oxime derivatives as potent cyclin-dependent kinase inhibitors with anticancer activity. J Med Chem 53:3696-706 CrossRef
    6. Connolly DJ, Cusack D, O’Sullivan TP, Guiry PJ (2005) Synthesis of quinazolinones and quinazolines. Tetrahedron 61:10153-0202 CrossRef
    7. Dandia A, Singh R (2005) Green chemical multi-component one-pot synthesis of fluorinated 2,3-disubstituted quinazolin-4(3 / H)-ones under solvent-free conditions and their anti-fungal activity. J Flourine Chem 126:307-12 CrossRef
    8. Dandia A, Arya K, Khaturia S, Jain AK (2010) Microwave-induced preparation of biologically important benzothiazolo[2,3- / b]quinazolines, and comparison with ultrasonic and classical heating. Monatsh Chem 141:979-85 CrossRef
    9. Ellis GP (2008) Chemistry of heterocyclic compounds: synthesis of fused heterocycles, vol 47. Wiley, New York
    10. El-Sherbeny MA (2000) Synthesis of certain pyrimido[2,1- / b]benzo-thiazole and benzothiazolo[2,3- / b]quinazoline derivatives for in vitro antitumor and antiviral activities. Arzneimittel-Forsch 50:848-53
    11. Gineinah MMM (2001) 6-, 7- and 8-(5-Aryl-1-phenyl- 2-pyrazolin-3-yl) imidazo- and pyrimido[2,1- / b]ben-zothiazoles as novel anticonvulsant agents. Sci Pharm 69:53-1
    12. Hameed A, Anwar A, Khan KM, Malik R, Shahab F, Siddiq S, Basha FZ, Choudhary MI (2013) Urease inhibition and anticancer activity of novel polyfunctional 5,6-dihydropyridine derivatives and their structure–activity relationship. Eur J Chem 4:49-2 CrossRef
    13. Jackman AL, Boyle FT, Harrap KR (1996) Tomudex?(ZD1694): from concept to care, a programme in rational drug discovery. Invest New Drug 14:305-16 CrossRef
    14. Lan P, Chen WN, Xiao GK, Sun PH, Chen WM (2010) 3D-QSAR and docking studies on pyrazolo[4,3- / h]qinazoline-3-carboxamides as cyclin-dependent kinase 2 (CDK2) inhibitors. Bioorg Med Chem Lett 20:6764-772 CrossRef
    15. Maritinez-Viturro CM, Dominguez D (2007) Synthesis of the antitumoural agent batracylin and related isoindolo[1,2- / b]quinazolin-12(10 / H)-ones. Tetrahedron Lett 48:1023-026 CrossRef
    16. Michael JP (1999) Quinoline, quinazoline and acridone alkaloids. Nat Prod Rep 16:697-09 CrossRef
    17. Michael JP (2002) Quinoline, quinazoline and acridone alkaloids. Nat Prod Rep 19:742-60 CrossRef
    18. Michael JP (2003) Quinoline, quinazoline and acridone alkaloids. Nat Prod Rep 20:476-93 CrossRef
    19. Noolvi MN, Patel HM, Kaur M (2012) Benzothiazoles: search for anticancer agents. Eur J Med Chem 54:447-62 CrossRef
    20. Sangshetti JN, Kokare ND, Kotharkar SA, Shinde DB (2008) ZrOCl2·8H2O catalyzed one-pot synthesis of 2,4,5-triaryl-1 / H-imidazoles and substituted 1,4-di(4,5-diphenylimidazol-yl)benzene. Chin Chem Lett 19:762-66 CrossRef
    21. Sangshetti JN, Chabukswar AR, Shinde DB (2011a) Microwave assisted one pot synthesis of some novel 2,5-disubstituted 1,3,4-oxadiazoles as antifungal agents. Bioorg Med Chem Lett 21:444-48 CrossRef
    22. Sangshetti JN, Lokwani DK, Sarkate AP, Shinde DB (2011b) Synthesis, antifungal activity, and docking study of some new 1,2,4-triazole analogs. Chem Biol Drug Des 78:800-80 CrossRef
    23. Suzuki Y, Oishi S, Takei Y, Yasue M, Misu R, Naoe S, Hou Z, Kure T, Nakanishi I, Ohno H, Hirasawa A, Tsujimoto G, Fujii N (2012) Design and synthesis of a novel class of CK2 inhibitors: application of copper- and gold-catalysed cascade reactions for fused nitrogen heterocycles. Org Biomol Chem 10:4907-915 CrossRef
    24. Tourouloglou N, Pazdur R (1996) Thymidylate synthase inhibitors. Clin Cancer Res 2:227-43
    25. Volzhina ON, Yakhontov LN (1982) Quinazoline cardiovascular agents (review). Pharm Chem J 16:734-38
    26. Witt A, Bergman J (2003) Recent developments in the field of quinazoline chemistry. Curr Org Chem 7:659-77 CrossRef
    27. Yevich JP, Temple DL, Covington RR, Owens DA, Seidehameland RJ, Dungan KW (1982) Antiallergics: 3-(1 / H-tetrazol-5-yl)-4 / H-pyrimido[2,1- / b]benzothiazol-4-ones. J Med Chem 25:864-68 CrossRef
  • 作者单位:Jaiprakash N. Sangshetti (1)
    Deepak K. Lokwani (2)
    Rashmi S. Chouthe (1)
    Ashok Ganure (3)
    Bhuvan Raval (4)
    Firoz A. Kalam Khan (1)
    Devanand B. Shinde (2)

    1. Y.B. Chavan College of Pharmacy, Dr. Rafiq Zakaria Campus, Aurangabad, 431 001, MS, India
    2. Department of Chemical Technology, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad, 31004, MS, India
    3. Sahyadri College of Pharmacy, Methwade, Sholapur, MS, India
    4. K. J. College of Pharmacy, Vadasma, Gujarat, India
  • ISSN:1554-8120
文摘
The simple, multicomponent, water-mediated synthesis of benzothiazolo [2,3-b] quinazolin-1-ones were carried out from aminobenzthiazoles, cyclic β diketone, and aromatic aldehydes. The simplicity, easy work up, short reaction time, and use of environmentally benign water as a solvent are some advantages of this proposed method. The newly synthesized compounds were evaluated for cytotoxicity against a panel of human cancer cell lines (U-937, Hep-2, vero, and MCF-7). Among the synthesized compounds, the compounds 4a and 4d showed higher anticancer activity. The result of DNA fragmentation analysis showed that the compound 4d induced dose-dependent apoptosis. This preliminary study encouraged us to consider the compounds 4a and 4d as interesting leads for further optimization.

© 2004-2018 中国地质图书馆版权所有 京ICP备05064691号 京公网安备11010802017129号

地址:北京市海淀区学院路29号 邮编:100083

电话:办公室:(+86 10)66554848;文献借阅、咨询服务、科技查新:66554700