Literature DB >> 35044579

Synthesis and in vitro evaluation of antitumor activity of spiro[indolo[2,1-b]quinazoline-pyrano[2,3-d]pyrimidine] and spiro[indolo[2,1-b]quinazoline-pyrido[2,3-d]pyrimidine] derivatives by using 2D and 3D cell culture models.

Zahra Sadeghian1, Mohammad Bayat2, Fatemeh Safari3.   

Abstract

Cancer as one of the biggest human health problems remains unsolved. The identification of novel platforms with the highest efficacy and low toxicity is a big challenge among interested researchers. In this regard, we are interested to synthesis and evaluate antitumor activity of spiro[indolo[2,1-b]quinazoline-pyrano[2,3-d]pyrimidine] and spiro[indolo[2,1-b]quinazoline-pyrido[2,3-d]pyrimidine] derivatives. The spiro heterocycles were synthesized via four-component reaction of isatoic anhydride, isatins, malononitrile, and some CH-acids including barbituric acid/thiobarbituric acid and 4(6)-aminouracil in CH2Cl2 under reflux condition. The significant features of this process are short reaction time, easy purification without chromatographic process, and high yields which make it attractive. Next, we employed 2D and 3D cell culture models to evaluate biological activity of our compounds. Our results showed that among our seven products (4a-g), the compounds 4a and 4e are the best with 50% growth inhibitory concentration (IC50) value lower than etoposide. Our results support this idea that the compounds 4a and 4e may be potential for drug designing in cancer therapy. However, more experiments will be required to find possible side effects of related compounds in vivo.
© 2022. The Author(s), under exclusive licence to Springer Nature Switzerland AG.

Entities:  

Keywords:  Antitumor activity; Indoloquinazoline; Isatin; Pyrano[2,3-d] pyrimidine; Spiro compounds; Tryptanthrin

Year:  2022        PMID: 35044579     DOI: 10.1007/s11030-022-10378-9

Source DB:  PubMed          Journal:  Mol Divers        ISSN: 1381-1991            Impact factor:   2.943


  16 in total

1.  Novel indolo[2,1-b]quinazoline analogues as cytostatic agents: synthesis, biological evaluation and structure-activity relationship.

Authors:  Vedula M Sharma; P Prasanna; K V Adi Seshu; B Renuka; C V Laxman Rao; G Sunil Kumar; C Prasad Narasimhulu; P Aravind Babu; R C Puranik; D Subramanyam; A Venkateswarlu; Sriram Rajagopal; K B Sunil Kumar; C Seshagiri Rao; N V S Rao Mamidi; Dhanvanthri S Deevi; R Ajaykumar; R Rajagopalan
Journal:  Bioorg Med Chem Lett       Date:  2002-09-02       Impact factor: 2.823

2.  Synthesis, biological evaluation and molecular docking study of 1,2,3-1H-triazoles having 4H-pyrano[2,3-d]pyrimidine as potential Mycobacterium tuberculosis protein tyrosine phosphatase B inhibitors.

Authors:  Nguyen Dinh Thanh; Do Son Hai; Nguyen Thi Thu Ha; Do Tien Tung; Cao Thi Le; Hoang Thi Kim Van; Vu Ngoc Toan; Duong Ngoc Toan; Le Hai Dang
Journal:  Bioorg Med Chem Lett       Date:  2018-12-06       Impact factor: 2.823

3.  Microwave-assisted synthesis of pyrimido[4,5-b][1,6]naphthyridin-4(3H)-ones with potential antitumor activity.

Authors:  Braulio Insuasty; Diana Becerra; Jairo Quiroga; Rodrigo Abonia; Manuel Nogueras; Justo Cobo
Journal:  Eur J Med Chem       Date:  2012-12-04       Impact factor: 6.514

4.  Synthesis of some novel pyrazolo[3,4-d]pyrimidine derivatives as potential antimicrobial agents.

Authors:  Bantwal Shivarama Holla; Manjathuru Mahalinga; Mari Sitambaram Karthikeyan; Padiyath Mohamed Akberali; Nalilu Sucheta Shetty
Journal:  Bioorg Med Chem       Date:  2005-11-28       Impact factor: 3.641

5.  Design, synthesis and in vitro evaluation of antitubercular and antimicrobial activity of some novel pyranopyrimidines.

Authors:  Nimesh R Kamdar; Dhaval D Haveliwala; Prashant T Mistry; Saurabh K Patel
Journal:  Eur J Med Chem       Date:  2010-08-12       Impact factor: 6.514

6.  1,8-Naphthyridines v. novel N-substituted 5-amino-N,N-diethyl-9-isopropyl [1,2,4]triazolo[4,3-a] [1,8]naphthyridine-6-carboxamides, as potent anti-inflammatory and/or analgesic agents completely devoid of acute gastrolesivity.

Authors:  Giancarlo Grossi; Mario Di Braccio; Giorgio Roma; Vigilio Ballabeni; Massimiliano Tognolini; Elisabetta Barocelli
Journal:  Eur J Med Chem       Date:  2005-02       Impact factor: 6.514

7.  Tryptanthrin derivatives as Toxoplasma gondii inhibitors--structure-activity-relationship of the 6-position.

Authors:  Bogdana Krivogorsky; Amber C Nelson; Kelsi A Douglas; Peter Grundt
Journal:  Bioorg Med Chem Lett       Date:  2012-12-20       Impact factor: 2.823

8.  Synthesis and antifungal activity of substituted 2,4,6-pyrimidinetrione carbaldehyde hydrazones.

Authors:  Donna M Neumann; Amy Cammarata; Gregory Backes; Glen E Palmer; Branko S Jursic
Journal:  Bioorg Med Chem       Date:  2013-12-12       Impact factor: 3.641

9.  Design, synthesis, and structure-activity relationship studies of tryptanthrins as antitubercular agents.

Authors:  Jae-Min Hwang; Taegwon Oh; Takushi Kaneko; Anna M Upton; Scott G Franzblau; Zhenkun Ma; Sang-Nae Cho; Pilho Kim
Journal:  J Nat Prod       Date:  2013-01-29       Impact factor: 4.050

10.  Microwave assisted one-pot catalyst free green synthesis of new methyl-7-amino-4-oxo-5-phenyl-2-thioxo-2,3,4,5-tetrahydro-1H-pyrano[2,3-d]pyrimidine-6-carboxylates as potent in vitro antibacterial and antifungal activity.

Authors:  Ajmal R Bhat; Aabid H Shalla; Rajendra S Dongre
Journal:  J Adv Res       Date:  2014-11-01       Impact factor: 10.479

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  2 in total

Review 1.  Insights into the recent progress in the medicinal chemistry of pyranopyrimidine analogs.

Authors:  Khaled M Elattar; Ayman Y El-Khateeb; Sahar E Hamed
Journal:  RSC Med Chem       Date:  2022-05-06

Review 2.  Recent advancements in the multicomponent synthesis of heterocycles integrated with a pyrano[2,3-d]pyrimidine core.

Authors:  Ayman Y El-Khateeb; Sahar E Hamed; Khaled M Elattar
Journal:  RSC Adv       Date:  2022-04-19       Impact factor: 4.036

  2 in total

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