title: Synthesis and tyrosinase inhibition activity of trans-stilbene derivatives.
abstract: Synthesis of a focussed library of trans-stilbene compounds through Wittig and other base catalysed condensation reactions is presented. The synthesized stilbenes were screened for their inhibitory potential against murine tyrosinase activity to explore the structure activity relationship (SAR). Presence of electron withdrawing group (-CN) at the double bond and hydroxyl group or halogen atom especially at para-position on the aromatic rings was found to significantly elevate the inhibitory activity. Among all the compounds screened, compounds 2, 6, 8, 10, 11, 15 and 21 were found to exhibit appreciable inhibitory activity. Compound 21 ((E)-2,3-bis(4-Hydroxyphenyl)acryonitrile) was found to be the most active with an IC50 value of 5.06 μM which is less than half of the value 10.78 μM observed for resveratrol (common standard used in murine tyrosinase activity studies) under similar conditions. The results obtained from the present study reveal structural/functional group sensitivity for the tyrosinase inhibitory activity of stilbenoid moieties and are expected to be very helpful for the design and synthesis of novel, selective and effective tyrosinase inhibitors.
authors.affiliation: Medicinal Chemistry Division, Indian Institute of Integrative Medicine, Jammu 180001, India. Electronic address: tabsismail@gmail.com.
authors.forename: Tabasum
authors.initials: T
authors.lastname: Ismail
authors.affiliation: Medicinal Chemistry Division, Indian Institute of Integrative Medicine, Jammu 180001, India; Department of Chemistry, Jamia Hamdard University, New Delhi 110062, India.
authors.forename: Syed
authors.initials: S
authors.lastname: Shafi
authors.affiliation: Vaccine Immunology Laboratory, NPC Division, Indian Institute of Chemical Technology, Hyderabad 500007, India.
authors.forename: Jada
authors.initials: J
authors.lastname: Srinivas
authors.affiliation: Combi. Chem. Bio Resource Center, Organic Chemistry Division, Dr. HomiBhabha Road, National Chemical Laboratory (NCL), Pune 411008, Maharastra, India.
authors.forename: Dhiman
authors.initials: D
authors.lastname: Sarkar
authors.affiliation: Cancer Pharmacology Division, Indian Institute of Integrative Medicine, Jammu 180001, India.
authors.forename: Yasrib
authors.initials: Y
authors.lastname: Qurishi
authors.affiliation: Medicinal Chemistry Division, Indian Institute of Integrative Medicine, Jammu 180001, India.
authors.forename: Jabeena
authors.initials: J
authors.lastname: Khazir
authors.affiliation: Department of Chemistry, Jamia Hamdard University, New Delhi 110062, India.
authors.forename: Mohammad Sarwar
authors.initials: MS
authors.lastname: Alam
authors.affiliation: Vaccine Immunology Laboratory, NPC Division, Indian Institute of Chemical Technology, Hyderabad 500007, India. Electronic address: hmskumar@gmail.com.
authors.forename: Halmuthur Mahabalarao Sampath
authors.initials: HM
authors.lastname: Kumar
mesh_terms: D000818:Animals; D045744:Cell Line, Tumor; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D051379:Mice; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors*; D000077185:Resveratrol; D013267:Stilbenes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: C000613603:2,3-bis(4-hydroxyphenyl)acrylonitrile; D004791:Enzyme Inhibitors; D013267:Stilbenes; D014442:Monophenol Monooxygenase; D000077185:Resveratrol
keywords: Electron withdrawing groups; Murine tyrosinase activity; Resveratrol; Stilbenoids; Tyrosinase inhibitors; Wittig reaction