Synthesis, characterization and anticancer evaluation of 2-(naphthalen-1-ylmethyl/naphthalen-2-yloxymethyl)-1-[5-(substituted phenyl)-[1,3,4]oxadiazol-2-ylmethyl]-1H-benzimidazole
In the present study o-phenylenediamine and naphtene-1-acetic acid/2-naphthoxyacetic acid were used as a starting material through a series of steps and 2-(naphthalen-1-ylmethyl/Naphthalen-2-yloxymethyl)-1H-benzimidazol-1-yl]acetohydrazide 5a, 5b were obtained. In the first series 1,3,4-oxadiazole d...
| Main Authors: | , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Elsevier
2014-09-01
|
| Series: | Arabian Journal of Chemistry |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S1878535213000312 |
| _version_ | 1818946265923190784 |
|---|---|
| author | Salahuddin Mohammad Shaharyar Avijit Mazumder Mohamed Jawed Ahsan |
| author_facet | Salahuddin Mohammad Shaharyar Avijit Mazumder Mohamed Jawed Ahsan |
| author_sort | Salahuddin |
| collection | DOAJ |
| description | In the present study o-phenylenediamine and naphtene-1-acetic acid/2-naphthoxyacetic acid were used as a starting material through a series of steps and 2-(naphthalen-1-ylmethyl/Naphthalen-2-yloxymethyl)-1H-benzimidazol-1-yl]acetohydrazide 5a, 5b were obtained. In the first series 1,3,4-oxadiazole derivatives have been synthesized from Schiff base of the corresponding hydrazide i.e. 2-[2-(naphthalen-1-ylmethyl)-1H-benzimidazol-1-yl]acetohydrazide 5a by using Chloramin-T. In the second series 1,3,4-oxadiazole has been synthesized from 2-{2-[(naphthalen-2-yloxy)methyl]-1Hbenzimidazol-1-yl}acetohydrazide 5b by using phosphorous oxychloride and aromatic acid. These compounds were evaluated by IR, NMR, Mass spectrometry, elemental analysis and finally in vitro anticancer evaluation was carried out by NCI 60 Cell screen at a single high dose (10–5 M) on various panel/cell lines. One compound 7c was found to be the most active on breast cancer cell line and compounds 4b and 7d were moderately active. |
| first_indexed | 2024-12-20T08:12:16Z |
| format | Article |
| id | doaj.art-befe316d6e6d4174b4d6e06ebb824383 |
| institution | Directory Open Access Journal |
| issn | 1878-5352 |
| language | English |
| last_indexed | 2024-12-20T08:12:16Z |
| publishDate | 2014-09-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Arabian Journal of Chemistry |
| spelling | doaj.art-befe316d6e6d4174b4d6e06ebb8243832022-12-21T19:47:14ZengElsevierArabian Journal of Chemistry1878-53522014-09-017441842410.1016/j.arabjc.2013.02.001Synthesis, characterization and anticancer evaluation of 2-(naphthalen-1-ylmethyl/naphthalen-2-yloxymethyl)-1-[5-(substituted phenyl)-[1,3,4]oxadiazol-2-ylmethyl]-1H-benzimidazoleSalahuddin0Mohammad Shaharyar1Avijit Mazumder2Mohamed Jawed Ahsan3Department of Pharmaceutical Technology, Noida Institute of Engineering and Technology, Knowledge Park-II, Greater Noida, Uttar Pradesh 201 306, IndiaDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Jamia Hamdard, New Delhi 110062, IndiaDepartment of Pharmaceutical Technology, Noida Institute of Engineering and Technology, Knowledge Park-II, Greater Noida, Uttar Pradesh 201 306, IndiaDepartment of Pharmaceutical Chemistry, Maharishi Arvind College of Pharmacy, Jaipur 302 023 Rajasthan, IndiaIn the present study o-phenylenediamine and naphtene-1-acetic acid/2-naphthoxyacetic acid were used as a starting material through a series of steps and 2-(naphthalen-1-ylmethyl/Naphthalen-2-yloxymethyl)-1H-benzimidazol-1-yl]acetohydrazide 5a, 5b were obtained. In the first series 1,3,4-oxadiazole derivatives have been synthesized from Schiff base of the corresponding hydrazide i.e. 2-[2-(naphthalen-1-ylmethyl)-1H-benzimidazol-1-yl]acetohydrazide 5a by using Chloramin-T. In the second series 1,3,4-oxadiazole has been synthesized from 2-{2-[(naphthalen-2-yloxy)methyl]-1Hbenzimidazol-1-yl}acetohydrazide 5b by using phosphorous oxychloride and aromatic acid. These compounds were evaluated by IR, NMR, Mass spectrometry, elemental analysis and finally in vitro anticancer evaluation was carried out by NCI 60 Cell screen at a single high dose (10–5 M) on various panel/cell lines. One compound 7c was found to be the most active on breast cancer cell line and compounds 4b and 7d were moderately active.http://www.sciencedirect.com/science/article/pii/S18785352130003121,3,4-OxadiazoleAnticancer evaluationBenzimidazole |
| spellingShingle | Salahuddin Mohammad Shaharyar Avijit Mazumder Mohamed Jawed Ahsan Synthesis, characterization and anticancer evaluation of 2-(naphthalen-1-ylmethyl/naphthalen-2-yloxymethyl)-1-[5-(substituted phenyl)-[1,3,4]oxadiazol-2-ylmethyl]-1H-benzimidazole Arabian Journal of Chemistry 1,3,4-Oxadiazole Anticancer evaluation Benzimidazole |
| title | Synthesis, characterization and anticancer evaluation of 2-(naphthalen-1-ylmethyl/naphthalen-2-yloxymethyl)-1-[5-(substituted phenyl)-[1,3,4]oxadiazol-2-ylmethyl]-1H-benzimidazole |
| title_full | Synthesis, characterization and anticancer evaluation of 2-(naphthalen-1-ylmethyl/naphthalen-2-yloxymethyl)-1-[5-(substituted phenyl)-[1,3,4]oxadiazol-2-ylmethyl]-1H-benzimidazole |
| title_fullStr | Synthesis, characterization and anticancer evaluation of 2-(naphthalen-1-ylmethyl/naphthalen-2-yloxymethyl)-1-[5-(substituted phenyl)-[1,3,4]oxadiazol-2-ylmethyl]-1H-benzimidazole |
| title_full_unstemmed | Synthesis, characterization and anticancer evaluation of 2-(naphthalen-1-ylmethyl/naphthalen-2-yloxymethyl)-1-[5-(substituted phenyl)-[1,3,4]oxadiazol-2-ylmethyl]-1H-benzimidazole |
| title_short | Synthesis, characterization and anticancer evaluation of 2-(naphthalen-1-ylmethyl/naphthalen-2-yloxymethyl)-1-[5-(substituted phenyl)-[1,3,4]oxadiazol-2-ylmethyl]-1H-benzimidazole |
| title_sort | synthesis characterization and anticancer evaluation of 2 naphthalen 1 ylmethyl naphthalen 2 yloxymethyl 1 5 substituted phenyl 1 3 4 oxadiazol 2 ylmethyl 1h benzimidazole |
| topic | 1,3,4-Oxadiazole Anticancer evaluation Benzimidazole |
| url | http://www.sciencedirect.com/science/article/pii/S1878535213000312 |
| work_keys_str_mv | AT salahuddin synthesischaracterizationandanticancerevaluationof2naphthalen1ylmethylnaphthalen2yloxymethyl15substitutedphenyl134oxadiazol2ylmethyl1hbenzimidazole AT mohammadshaharyar synthesischaracterizationandanticancerevaluationof2naphthalen1ylmethylnaphthalen2yloxymethyl15substitutedphenyl134oxadiazol2ylmethyl1hbenzimidazole AT avijitmazumder synthesischaracterizationandanticancerevaluationof2naphthalen1ylmethylnaphthalen2yloxymethyl15substitutedphenyl134oxadiazol2ylmethyl1hbenzimidazole AT mohamedjawedahsan synthesischaracterizationandanticancerevaluationof2naphthalen1ylmethylnaphthalen2yloxymethyl15substitutedphenyl134oxadiazol2ylmethyl1hbenzimidazole |