Synthetic modification of dehydrozingerone and their biological evaluation for anti-tubercular and anti-inflammatory potency
The current research effort focuses on dehydrozingerone (DHZ, 1), a secondary metabolite discovered in the rhizome of Zingiber officinale. Here, we designed and synthesized the diaryl ether derivatives in high yields (80–93%) using substituted arylboronic acids and copper-promoted arylation of pheno...
| Main Authors: | , , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Elsevier
2023-01-01
|
| Series: | Results in Chemistry |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S221171562300173X |
| _version_ | 1797799038366515200 |
|---|---|
| author | Chetan Kumar Mohamad Mosa Mubarak Chetan Paul Singh Narendra Chauhan N.K. Satti Govind Yadav Ram A Vishwakarma Zahoor Ahmad Parry Asif Ali |
| author_facet | Chetan Kumar Mohamad Mosa Mubarak Chetan Paul Singh Narendra Chauhan N.K. Satti Govind Yadav Ram A Vishwakarma Zahoor Ahmad Parry Asif Ali |
| author_sort | Chetan Kumar |
| collection | DOAJ |
| description | The current research effort focuses on dehydrozingerone (DHZ, 1), a secondary metabolite discovered in the rhizome of Zingiber officinale. Here, we designed and synthesized the diaryl ether derivatives in high yields (80–93%) using substituted arylboronic acids and copper-promoted arylation of phenol. For anti-microbial activity against clinically significant infectious strains of Mycobacterium tuberculosis (ATCC 27294) and H37Ra (ATCC 25177), as well as against Gram-positive and Gram-negative bacteria (B. subtilis ATCC 6633, E. faecalis ATCC 29212, P. aeruginosa ATCC 9027, Escherichia coli ATCC 11105). 16 g/ml MIC value and mycobacterial potential. Compound 7 was the most active of all the compounds, with a MIC Value of 4 g/ml. Additionally, pro-inflammatory cytokines were checked for across the board in the compounds (1–16). IL6 and TNF- are produced by LPS-stimulated RAW 264.7 cells in a dose-dependent manner. |
| first_indexed | 2024-03-13T04:13:56Z |
| format | Article |
| id | doaj.art-c5d9b5aa433c4c7488280d7f457faee6 |
| institution | Directory Open Access Journal |
| issn | 2211-7156 |
| language | English |
| last_indexed | 2024-03-13T04:13:56Z |
| publishDate | 2023-01-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Results in Chemistry |
| spelling | doaj.art-c5d9b5aa433c4c7488280d7f457faee62023-06-21T06:52:38ZengElsevierResults in Chemistry2211-71562023-01-015100934Synthetic modification of dehydrozingerone and their biological evaluation for anti-tubercular and anti-inflammatory potencyChetan Kumar0Mohamad Mosa Mubarak1Chetan Paul Singh2Narendra Chauhan3N.K. Satti4Govind Yadav5Ram A Vishwakarma6Zahoor Ahmad Parry7Asif Ali8Natural Product Medicinal Chemistry Division, CSIR-Indian Institute of Integrative Medicine, Canal Road, Jammu 180001, India; Academy of Scientific & Innovative Research (AcSIR), Anusandhan Bhawan, 2 Rafi Marg, New Delhi 110001, IndiaClinical Microbiology and PK-PD Division, CSIR-IIIM, Sanatnagar, Srinagar (J&K) 190005, India; Academy of Scientific & Innovative Research (AcSIR), Anusandhan Bhawan, 2 Rafi Marg, New Delhi 110001, IndiaNatural Product Medicinal Chemistry Division, CSIR-Indian Institute of Integrative Medicine, Canal Road, Jammu 180001, India; Academy of Scientific & Innovative Research (AcSIR), Anusandhan Bhawan, 2 Rafi Marg, New Delhi 110001, IndiaInvivo Laboratory for Drug Discovery, Pharmacology Division, CSIR-Indian Institute of Integrative Medicine, Canal Road, Jammu 180001, India; Academy of Scientific & Innovative Research (AcSIR), Anusandhan Bhawan, 2 Rafi Marg, New Delhi 110001, IndiaNatural Product Medicinal Chemistry Division, CSIR-Indian Institute of Integrative Medicine, Canal Road, Jammu 180001, India; Academy of Scientific & Innovative Research (AcSIR), Anusandhan Bhawan, 2 Rafi Marg, New Delhi 110001, IndiaInvivo Laboratory for Drug Discovery, Pharmacology Division, CSIR-Indian Institute of Integrative Medicine, Canal Road, Jammu 180001, India; Academy of Scientific & Innovative Research (AcSIR), Anusandhan Bhawan, 2 Rafi Marg, New Delhi 110001, IndiaNatural Product Medicinal Chemistry Division, CSIR-Indian Institute of Integrative Medicine, Canal Road, Jammu 180001, India; Academy of Scientific & Innovative Research (AcSIR), Anusandhan Bhawan, 2 Rafi Marg, New Delhi 110001, IndiaClinical Microbiology and PK-PD Division, CSIR-IIIM, Sanatnagar, Srinagar (J&K) 190005, India; Academy of Scientific & Innovative Research (AcSIR), Anusandhan Bhawan, 2 Rafi Marg, New Delhi 110001, IndiaNatural Product Medicinal Chemistry Division, CSIR-Indian Institute of Integrative Medicine, Canal Road, Jammu 180001, India; Academy of Scientific & Innovative Research (AcSIR), Anusandhan Bhawan, 2 Rafi Marg, New Delhi 110001, India; Medicinal & Process Chemistry Division, CSIR-Central Drug Research Institute (CDRI), Sector 10, Jankipuram Extension, Sitapur Road, Lucknow 226031, India; Corresponding author at: Medicinal & Process Chemistry Division, CSIR-Central Drug Research Institute (CDRI), Sector 10, Jankipuram Extension, Sitapur Road, Lucknow 226031, India.The current research effort focuses on dehydrozingerone (DHZ, 1), a secondary metabolite discovered in the rhizome of Zingiber officinale. Here, we designed and synthesized the diaryl ether derivatives in high yields (80–93%) using substituted arylboronic acids and copper-promoted arylation of phenol. For anti-microbial activity against clinically significant infectious strains of Mycobacterium tuberculosis (ATCC 27294) and H37Ra (ATCC 25177), as well as against Gram-positive and Gram-negative bacteria (B. subtilis ATCC 6633, E. faecalis ATCC 29212, P. aeruginosa ATCC 9027, Escherichia coli ATCC 11105). 16 g/ml MIC value and mycobacterial potential. Compound 7 was the most active of all the compounds, with a MIC Value of 4 g/ml. Additionally, pro-inflammatory cytokines were checked for across the board in the compounds (1–16). IL6 and TNF- are produced by LPS-stimulated RAW 264.7 cells in a dose-dependent manner.http://www.sciencedirect.com/science/article/pii/S221171562300173XDehydrozingeroneCopper-promoted arylationDiaryl derivativesAnti-tubercular and anti-inflammatory activity |
| spellingShingle | Chetan Kumar Mohamad Mosa Mubarak Chetan Paul Singh Narendra Chauhan N.K. Satti Govind Yadav Ram A Vishwakarma Zahoor Ahmad Parry Asif Ali Synthetic modification of dehydrozingerone and their biological evaluation for anti-tubercular and anti-inflammatory potency Results in Chemistry Dehydrozingerone Copper-promoted arylation Diaryl derivatives Anti-tubercular and anti-inflammatory activity |
| title | Synthetic modification of dehydrozingerone and their biological evaluation for anti-tubercular and anti-inflammatory potency |
| title_full | Synthetic modification of dehydrozingerone and their biological evaluation for anti-tubercular and anti-inflammatory potency |
| title_fullStr | Synthetic modification of dehydrozingerone and their biological evaluation for anti-tubercular and anti-inflammatory potency |
| title_full_unstemmed | Synthetic modification of dehydrozingerone and their biological evaluation for anti-tubercular and anti-inflammatory potency |
| title_short | Synthetic modification of dehydrozingerone and their biological evaluation for anti-tubercular and anti-inflammatory potency |
| title_sort | synthetic modification of dehydrozingerone and their biological evaluation for anti tubercular and anti inflammatory potency |
| topic | Dehydrozingerone Copper-promoted arylation Diaryl derivatives Anti-tubercular and anti-inflammatory activity |
| url | http://www.sciencedirect.com/science/article/pii/S221171562300173X |
| work_keys_str_mv | AT chetankumar syntheticmodificationofdehydrozingeroneandtheirbiologicalevaluationforantitubercularandantiinflammatorypotency AT mohamadmosamubarak syntheticmodificationofdehydrozingeroneandtheirbiologicalevaluationforantitubercularandantiinflammatorypotency AT chetanpaulsingh syntheticmodificationofdehydrozingeroneandtheirbiologicalevaluationforantitubercularandantiinflammatorypotency AT narendrachauhan syntheticmodificationofdehydrozingeroneandtheirbiologicalevaluationforantitubercularandantiinflammatorypotency AT nksatti syntheticmodificationofdehydrozingeroneandtheirbiologicalevaluationforantitubercularandantiinflammatorypotency AT govindyadav syntheticmodificationofdehydrozingeroneandtheirbiologicalevaluationforantitubercularandantiinflammatorypotency AT ramavishwakarma syntheticmodificationofdehydrozingeroneandtheirbiologicalevaluationforantitubercularandantiinflammatorypotency AT zahoorahmadparry syntheticmodificationofdehydrozingeroneandtheirbiologicalevaluationforantitubercularandantiinflammatorypotency AT asifali syntheticmodificationofdehydrozingeroneandtheirbiologicalevaluationforantitubercularandantiinflammatorypotency |