Synthesis, characterization and cytotoxic investigations of novel bis(indole) analogues besides antimicrobial study
Two series of novel bis(indole) analogues viz., N′-((5-substituted-1H-indol-3-yl)methylene)-n-(1H-indol-3-yl)alkanehydrazides (7a–f) and N′-((5-substituted-1-(3-methylbut-2-enyl)-1H-indol-3-yl)methylene)-n-(1H-indol-3-yl)acetohydrazide (8a–f) were synthesized and characterized by spectral analysis....
| Main Authors: | , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Elsevier
2019-12-01
|
| Series: | Arabian Journal of Chemistry |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S187853521500163X |
| _version_ | 1818503739700412416 |
|---|---|
| author | Praveen Choppara M.S. Bethu Y. Vara Prasad J. Venkateswara Rao T.J. Uday Ranjan G.V. Siva Prasad Rajitha Doradla Y.L.N. Murthy |
| author_facet | Praveen Choppara M.S. Bethu Y. Vara Prasad J. Venkateswara Rao T.J. Uday Ranjan G.V. Siva Prasad Rajitha Doradla Y.L.N. Murthy |
| author_sort | Praveen Choppara |
| collection | DOAJ |
| description | Two series of novel bis(indole) analogues viz., N′-((5-substituted-1H-indol-3-yl)methylene)-n-(1H-indol-3-yl)alkanehydrazides (7a–f) and N′-((5-substituted-1-(3-methylbut-2-enyl)-1H-indol-3-yl)methylene)-n-(1H-indol-3-yl)acetohydrazide (8a–f) were synthesized and characterized by spectral analysis. The target molecules were screened for their antimicrobial, anticancer activities and structure and activity relationship (SAR) was investigated. Compounds 7a, 7c and 8a were found to be active in antimicrobial screening. Anticancer screening reveals that Compound 7c was active against HeLa cell line with an IC50 of 43.1 μM and compound 7d was found to be interesting candidate with an IC50 of 26.0 and 30.2 μM against Colo-205 and Hep G2 cell lines respectively. Keywords: Indole-3-acylhydrazides, Indole-3-carboxaldehyde, N-prenylated indole-3-carboxaldehyde, Bis(indole) analogues, Antimicrobial activity, Anticancer activity |
| first_indexed | 2024-12-10T21:27:59Z |
| format | Article |
| id | doaj.art-e0a952fdcbd742d0881176a2b49ead73 |
| institution | Directory Open Access Journal |
| issn | 1878-5352 |
| language | English |
| last_indexed | 2024-12-10T21:27:59Z |
| publishDate | 2019-12-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Arabian Journal of Chemistry |
| spelling | doaj.art-e0a952fdcbd742d0881176a2b49ead732022-12-22T01:32:56ZengElsevierArabian Journal of Chemistry1878-53522019-12-0112827212731Synthesis, characterization and cytotoxic investigations of novel bis(indole) analogues besides antimicrobial studyPraveen Choppara0M.S. Bethu1Y. Vara Prasad2J. Venkateswara Rao3T.J. Uday Ranjan4G.V. Siva Prasad5Rajitha Doradla6Y.L.N. Murthy7Department of Organic Chemistry, Foods, Drugs & Water, Andhra University, Visakhapatnam 530 003, India; Department of Science & Humanities, Raghu Engineering College, Dakamarri, Visakhapatnam 531 162, IndiaBiology Division, Indian Institute of Chemical Technology, Hyderabad 500 007, IndiaDepartment of Organic Chemistry, Foods, Drugs & Water, Andhra University, Visakhapatnam 530 003, IndiaBiology Division, Indian Institute of Chemical Technology, Hyderabad 500 007, IndiaDepartment of Marine Living Resources, Andhra University, Visakhapatnam 530 003, IndiaDepartment of Organic Chemistry, Foods, Drugs & Water, Andhra University, Visakhapatnam 530 003, India; Department of Science & Humanities, Raghu Engineering College, Dakamarri, Visakhapatnam 531 162, IndiaDepartment of Organic Chemistry, Foods, Drugs & Water, Andhra University, Visakhapatnam 530 003, IndiaDepartment of Organic Chemistry, Foods, Drugs & Water, Andhra University, Visakhapatnam 530 003, India; Corresponding author. Tel.: +91 9849229804; fax: +91 891 2713813.Two series of novel bis(indole) analogues viz., N′-((5-substituted-1H-indol-3-yl)methylene)-n-(1H-indol-3-yl)alkanehydrazides (7a–f) and N′-((5-substituted-1-(3-methylbut-2-enyl)-1H-indol-3-yl)methylene)-n-(1H-indol-3-yl)acetohydrazide (8a–f) were synthesized and characterized by spectral analysis. The target molecules were screened for their antimicrobial, anticancer activities and structure and activity relationship (SAR) was investigated. Compounds 7a, 7c and 8a were found to be active in antimicrobial screening. Anticancer screening reveals that Compound 7c was active against HeLa cell line with an IC50 of 43.1 μM and compound 7d was found to be interesting candidate with an IC50 of 26.0 and 30.2 μM against Colo-205 and Hep G2 cell lines respectively. Keywords: Indole-3-acylhydrazides, Indole-3-carboxaldehyde, N-prenylated indole-3-carboxaldehyde, Bis(indole) analogues, Antimicrobial activity, Anticancer activityhttp://www.sciencedirect.com/science/article/pii/S187853521500163X |
| spellingShingle | Praveen Choppara M.S. Bethu Y. Vara Prasad J. Venkateswara Rao T.J. Uday Ranjan G.V. Siva Prasad Rajitha Doradla Y.L.N. Murthy Synthesis, characterization and cytotoxic investigations of novel bis(indole) analogues besides antimicrobial study Arabian Journal of Chemistry |
| title | Synthesis, characterization and cytotoxic investigations of novel bis(indole) analogues besides antimicrobial study |
| title_full | Synthesis, characterization and cytotoxic investigations of novel bis(indole) analogues besides antimicrobial study |
| title_fullStr | Synthesis, characterization and cytotoxic investigations of novel bis(indole) analogues besides antimicrobial study |
| title_full_unstemmed | Synthesis, characterization and cytotoxic investigations of novel bis(indole) analogues besides antimicrobial study |
| title_short | Synthesis, characterization and cytotoxic investigations of novel bis(indole) analogues besides antimicrobial study |
| title_sort | synthesis characterization and cytotoxic investigations of novel bis indole analogues besides antimicrobial study |
| url | http://www.sciencedirect.com/science/article/pii/S187853521500163X |
| work_keys_str_mv | AT praveenchoppara synthesischaracterizationandcytotoxicinvestigationsofnovelbisindoleanaloguesbesidesantimicrobialstudy AT msbethu synthesischaracterizationandcytotoxicinvestigationsofnovelbisindoleanaloguesbesidesantimicrobialstudy AT yvaraprasad synthesischaracterizationandcytotoxicinvestigationsofnovelbisindoleanaloguesbesidesantimicrobialstudy AT jvenkateswararao synthesischaracterizationandcytotoxicinvestigationsofnovelbisindoleanaloguesbesidesantimicrobialstudy AT tjudayranjan synthesischaracterizationandcytotoxicinvestigationsofnovelbisindoleanaloguesbesidesantimicrobialstudy AT gvsivaprasad synthesischaracterizationandcytotoxicinvestigationsofnovelbisindoleanaloguesbesidesantimicrobialstudy AT rajithadoradla synthesischaracterizationandcytotoxicinvestigationsofnovelbisindoleanaloguesbesidesantimicrobialstudy AT ylnmurthy synthesischaracterizationandcytotoxicinvestigationsofnovelbisindoleanaloguesbesidesantimicrobialstudy |