Synthesis and cytotoxic evaluation of novel quinozalinone derivatives with substituted benzimidazole in position 3
Quinazolinone and benzimidazole are both fused heterocyclic compounds which have shown valuable biological properties including cytotoxic, antibacterial, and antifungal activities. In this study, a series of novel quinazolinone derivatives substituted with benzimidazole were synthesized in two parts...
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Wolters Kluwer Medknow Publications
2019-01-01
|
| Series: | Research in Pharmaceutical Sciences |
| Subjects: | |
| Online Access: | http://www.rpsjournal.net/article.asp?issn=1735-5362;year=2019;volume=14;issue=3;spage=247;epage=254;aulast=Taherian |
| _version_ | 1818864610791391232 |
|---|---|
| author | Elham Taherian Ghadamali Khodarahmi Marzieh Khajouei Farshid Hassanzadeh Nasim Dana |
| author_facet | Elham Taherian Ghadamali Khodarahmi Marzieh Khajouei Farshid Hassanzadeh Nasim Dana |
| author_sort | Elham Taherian |
| collection | DOAJ |
| description | Quinazolinone and benzimidazole are both fused heterocyclic compounds which have shown valuable biological properties including cytotoxic, antibacterial, and antifungal activities. In this study, a series of novel quinazolinone derivatives substituted with benzimidazole were synthesized in two parts. In the first part 2 - phenyl - 1H - benzimidazol - 6 - amine (4) was synthesized from the reaction of 4-nitro-o-phenylenediamine and benzoic acid. In the second part, new 3-(2-phenyl-1H benzoimidazol-5-yl)- 3H-quinazolin-4-one derivatives (8a-8f) were also prepared. Finally compound 4 was reacted with the different benzoxazinone derivatives (8a-8f) to give the target compounds. The structures of the synthesized compounds were confirmed by IR and 1HNMR. Cytotoxic activities of the final compounds were assessed at 100, 200, 300, 400, and 500 μM against MCF-7 and HeLa cell lines using the MTT colorimetric assay. Almost all compounds exhibited good cytotoxic activity against both cell lines. Compound 9d demonstrated the highest cytotoxic activity against MCF7 and Hela cell lines with IC50 70 μM and 50 μM, respectively. |
| first_indexed | 2024-12-19T10:34:24Z |
| format | Article |
| id | doaj.art-6eeda0a337334eeaa46882d6ff40da3b |
| institution | Directory Open Access Journal |
| issn | 1735-5362 1735-9414 |
| language | English |
| last_indexed | 2024-12-19T10:34:24Z |
| publishDate | 2019-01-01 |
| publisher | Wolters Kluwer Medknow Publications |
| record_format | Article |
| series | Research in Pharmaceutical Sciences |
| spelling | doaj.art-6eeda0a337334eeaa46882d6ff40da3b2022-12-21T20:25:39ZengWolters Kluwer Medknow PublicationsResearch in Pharmaceutical Sciences1735-53621735-94142019-01-0114324725410.4103/1735-5362.258493Synthesis and cytotoxic evaluation of novel quinozalinone derivatives with substituted benzimidazole in position 3Elham TaherianGhadamali KhodarahmiMarzieh KhajoueiFarshid HassanzadehNasim DanaQuinazolinone and benzimidazole are both fused heterocyclic compounds which have shown valuable biological properties including cytotoxic, antibacterial, and antifungal activities. In this study, a series of novel quinazolinone derivatives substituted with benzimidazole were synthesized in two parts. In the first part 2 - phenyl - 1H - benzimidazol - 6 - amine (4) was synthesized from the reaction of 4-nitro-o-phenylenediamine and benzoic acid. In the second part, new 3-(2-phenyl-1H benzoimidazol-5-yl)- 3H-quinazolin-4-one derivatives (8a-8f) were also prepared. Finally compound 4 was reacted with the different benzoxazinone derivatives (8a-8f) to give the target compounds. The structures of the synthesized compounds were confirmed by IR and 1HNMR. Cytotoxic activities of the final compounds were assessed at 100, 200, 300, 400, and 500 μM against MCF-7 and HeLa cell lines using the MTT colorimetric assay. Almost all compounds exhibited good cytotoxic activity against both cell lines. Compound 9d demonstrated the highest cytotoxic activity against MCF7 and Hela cell lines with IC50 70 μM and 50 μM, respectively.http://www.rpsjournal.net/article.asp?issn=1735-5362;year=2019;volume=14;issue=3;spage=247;epage=254;aulast=Taheriancytotoxicity; benzimidazole; mtt assay; quinazolinone. |
| spellingShingle | Elham Taherian Ghadamali Khodarahmi Marzieh Khajouei Farshid Hassanzadeh Nasim Dana Synthesis and cytotoxic evaluation of novel quinozalinone derivatives with substituted benzimidazole in position 3 Research in Pharmaceutical Sciences cytotoxicity; benzimidazole; mtt assay; quinazolinone. |
| title | Synthesis and cytotoxic evaluation of novel quinozalinone derivatives with substituted benzimidazole in position 3 |
| title_full | Synthesis and cytotoxic evaluation of novel quinozalinone derivatives with substituted benzimidazole in position 3 |
| title_fullStr | Synthesis and cytotoxic evaluation of novel quinozalinone derivatives with substituted benzimidazole in position 3 |
| title_full_unstemmed | Synthesis and cytotoxic evaluation of novel quinozalinone derivatives with substituted benzimidazole in position 3 |
| title_short | Synthesis and cytotoxic evaluation of novel quinozalinone derivatives with substituted benzimidazole in position 3 |
| title_sort | synthesis and cytotoxic evaluation of novel quinozalinone derivatives with substituted benzimidazole in position 3 |
| topic | cytotoxicity; benzimidazole; mtt assay; quinazolinone. |
| url | http://www.rpsjournal.net/article.asp?issn=1735-5362;year=2019;volume=14;issue=3;spage=247;epage=254;aulast=Taherian |
| work_keys_str_mv | AT elhamtaherian synthesisandcytotoxicevaluationofnovelquinozalinonederivativeswithsubstitutedbenzimidazoleinposition3 AT ghadamalikhodarahmi synthesisandcytotoxicevaluationofnovelquinozalinonederivativeswithsubstitutedbenzimidazoleinposition3 AT marziehkhajouei synthesisandcytotoxicevaluationofnovelquinozalinonederivativeswithsubstitutedbenzimidazoleinposition3 AT farshidhassanzadeh synthesisandcytotoxicevaluationofnovelquinozalinonederivativeswithsubstitutedbenzimidazoleinposition3 AT nasimdana synthesisandcytotoxicevaluationofnovelquinozalinonederivativeswithsubstitutedbenzimidazoleinposition3 |