117886-49-4Relevant academic research and scientific papers
Synthesis, characterizations, biological activities and docking studies of novel dihydroxy derivatives of natural phenolic monoterpenoids containing azomethine linkage
Rajput, Jamatsing D.,Bagul, Suresh D.,Hosamani, Amar A.,Patil, Manohar M.,Bendre, Ratnamala S.
, p. 5377 - 5393 (2017/09/23)
Abstract: In the present work, we report the synthesis of six new azomethine linkage containing dihydroxy derivatives of carvacrol, thymol, and eugenol. All the synthesized derivatives have been characterized by spectroscopic techniques and their structures were confirmed by X-ray single crystallography. Synthesized derivatives were screened for anti-oxidant activity using DPPH radical scavenging assay, and anticancer activity by using SRB assay against pancreatic cancer with MIAPaCa-2 and colon cancer with HCT-15 cell lines. The molecular docking studies of all the synthesized derivatives were performed on cyclooxygenases (COX-2) protein enzyme. In the anti-oxidant test, the values of EC50 indicated that all the compounds show excellent anti-oxidant potency, and similarly the GI50 values in anticancer tests indicated that most of the compounds possess good anticancer efficacy. The overall docking score suggested that all the synthesized compounds exhibit good binding affinity towards cyclooxygenases (COX-2) protein enzyme.
The Diels-Alder reactions of para-benzoquinone nitrogen-derivatives: An experimental and theoretical study
Uliana, Marciana P.,Servilha, Bruno M.,Alexopoulos, Olga,De Oliveira, Kleber T.,Tormena, Cláudio F.,Ferreira, Marco A.B.,Brocksom, Timothy J.
, p. 6963 - 6973 (2015/11/09)
An experimental and theoretical study of the comparative reactivity and selectivity of the Diels-Alder reactions of para-benzoquinones and three nitrogen derivatives have been performed. The mono-oximes derivatives do not react under the tested reaction conditions, whereas the tosylated mono-oximes react slowly. However, the mono N-tosyl imines show excellent reactivity, and superior to the parent parabenzoquinones. DFT calculations support these experimental results.
Synthesis and antioxidant activity of thymol and carvacrol based Schiff bases
Beena,Kumar, Deepak,Rawat, Diwan S.
, p. 641 - 645 (2013/03/13)
Thymol and carvacrol are well known antioxidants found in the extract of the plants of thyme species. The Schiff bases of 2-iso-propyl-5-methyl-phenol (thymol/1a), 2-tert-butyl-5-methyl-phenol (1b) and 5-iso-propyl-2-methyl-phenol (carvacrol/1c) exhibited much better antioxidant activity than thymol and carvacrol in DPPH assay. Ten compounds (4k, 4l, 4r, 5k, 5l, 5q, 5r, 6k, 6l and 6r) showed better or similar activity as compared to the reference compound ascorbic acid. Twenty-four most active compounds were also screened by ABTS method and showed 60-90% inhibition at 5 μg/mL concentration.
Hybrid molecules of carvacrol and benzoyl urea/thiourea with potential applications in agriculture and medicine
Pete, Umesh D.,Zade, Chetan M.,Bhosale, Jitendra D.,Tupe, Santosh G.,Chaudhary, Preeti M.,Dikundwar, Amol G.,Bendre, Ratnamala S.
, p. 5550 - 5554 (2012/09/22)
Benzoyl phenyl urea, a class of insect growth regulator's acts by inhibiting chitin synthesis. Carvacrol, a naturally occurring monoterpenoid is an effective antifungal agent. We have structurally modified carvacrol (2-methyl-5-[1-methylethyl] phenol) by introducing benzoylphenyl urea linkage. Two series of benzoylcarvacryl thiourea (BCTU, 4a-f) and benzoylcarvacryl urea (BCU, 5a-f) derivatives were prepared and characterized by elemental analysis, IR, 1H and 13C NMR and Mass spectroscopy. Derivatives 4b, 4d, 4e, 4f and 5d, 5f showed comparable insecticidal activity with the standard BPU lufenuron against Dysdercus koenigii. BCTU derivatives 4c, 4e and BCU 5c showed good antifungal activity against phytopathogenic fungi viz. Magnaporthe grisae, Fusarium oxysporum, Dreschlera oryzae; food spoilage yeasts viz. Debaromyces hansenii, Pichia membranifaciens; and human pathogens viz. Candida albicans and Cryptococcus neoformans. Compounds 5d, 5e and 5f showed potent activity against human pathogens. Moderate and selective activity was observed for other compounds. All the synthesized compounds were non-haemolytic. These compounds have potential application in agriculture and medicine.
