title: Synthesis and anticancer activity of some novel 5,6-fused hybrids of juglone based 1,4-naphthoquinones.
abstract: Six novel 5,6-fused hybrids such as dihydrobenzofuran-quinone (4a and 4b), benzofuran-quinone (5a and 5b) and chromene-quinone (6a and 6b) of juglone based 1,4-naphthoquinones were synthesized by employing a three step protocol with the cyclisation of o-allyl phenol as the key step. The anticancer activity of the newly synthesized compounds was evaluated in vitro against seven human cancer cell lines including cervix (ME-180 and HeLa), breast (MCF-7, MDA-MB-453 and MDA-MB-231), prostate (PC-3) and colon (HT-29) by using MTT assay. The screening results showed that majority of the synthesized compounds exhibited significant anticancer activity. In particular, compounds 6a and 6b showed potent activities than the standard drug etoposide against prostate and breast cancer cell lines respectively. Flow cytometric analysis revealed that compounds 6a and 6b induced apoptosis and arrested the cell cycle at G2/M phase in PC-3 and MDA-MB-453 cells respectively.
authors: Natural Products Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India. Electronic address: uvmavadani@yahoo.com.
authors: Uppuluri Venkata
authors: UV
authors: Mallavadhani
authors: Natural Products Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India.
authors: Chakka Vara
authors: CV
authors: Prasad
authors: Department of Pharmacology & Toxicology, National Institute of Pharmaceutical Education& Research, Hyderabad 500037, India.
authors: Shweta
authors: S
authors: Shrivastava
authors: Department of Pharmacology & Toxicology, National Institute of Pharmaceutical Education& Research, Hyderabad 500037, India.
authors: V G M
authors: VG
authors: Naidu
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D017209:Apoptosis / Q000187:drug effects; D002453:Cell Cycle / Q000187:drug effects; D045744:Cell Line, Tumor; D060326:Chemistry Techniques, Synthetic; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D009285:Naphthoquinones / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology*
chemical_list: D000970:Antineoplastic Agents; D009285:Naphthoquinones; C035342:1,4-naphthoquinone; C005134:juglone
keywords: Anticancer activity; Apoptosis; Cell cycle arrest; Juglone; Plumbagin