5543-37-3Relevant articles and documents
Copper-catalyzed direct coupling of benzoxazin-2-ones with indoles for the synthesis of diverse 3-indolylbenzoxazin-2-ones: Access to natural cephalandole A
Pandit, Rameshwar Prasad,Shim, Jae-Jin,Kim, Sung Hong,Lee, Yong Rok
, p. 55288 - 55295 (2017)
A novel and facile copper-catalyzed direct coupling for the synthesis of diverse and functionalized 3-indolyl benzoxazin-2-ones from benzoxazin-2-ones and indoles has been developed. This newmethodology offers an easy and rapid approach to a variety of 3-indolylbenzo[b][1,4]oxazin-2-ones in high yield. As an application of this protocol, a gram-scale synthesis of naturally occurring cephalandole A has also been accomplished.
An efficient synthesis and biological evaluation of novel analogues of natural product Cephalandole A: A new class of antimicrobial and antiplatelet agents
Sharma, Vashundhra,Jaiswal, Pradeep K.,Kumar, Krishan,Saran, Mukesh,Mathur, Manas,Swami, Ajit K.,Chaudhary, Sandeep
, p. 13 - 19 (2018/06/20)
Cephalandole A 2, a small indole alkaloid isolated from the Taiwanese orchid Cephalanceropsis gracilis (Orchidaceae), exhibits anticancer activity. Surprisingly, this natural product has not been evaluated for any other biological activity so far. To discover other novel potential of Cephalandole A 2, an efficient and economic synthetic protocol for novel Cephalandole A analogues 21a-o has been developed, in only 3 steps from using indole, and applied for their biological activity. Biological testing showed that Cephalandole A 2 and its novel analogues 21a-o exhibited potential antimicrobial and antiplatelet activity in preliminary assay. To the best of our knowledge, this is the first report of Cephalandole A 2 and its novel synthetic analogues 21a-o as a new class of antimicrobial and antiplatelet agents. In this study, 2 and other analogues i.e., 21b, 21d, 21i and 21o showed promising antimicrobial activity against the phytopathogenic bacteria and fungi. Cephalandole A 2, 21c, 21f and 21i, also showed potent antiplatelet activity.
Microwave-assisted one-pot efficient synthesis of functionalized 2-oxo-2-phenylethylidenes-linked 2-oxobenzo[1, 4]oxazines and 2-oxoquino[1, 4]oxalines: Synthetic applications, antioxidant activity, SAR and cytotoxic studies
Sharma, Vashundhra,Jaiswal, Pradeep K.,Yadav, Dharmendra K.,Saran, Mukesh,Prikhodko, Jaroslav,Mathur, Manas,Swami, Ajit K.,Mashevskaya, Irina V.,Chaudhary, Sandeep
, p. 988 - 1004 (2018/01/17)
A microwave-assisted, environmentally benign green protocol for the synthesis of functionalized (Z)-3-(2-oxo-2-phenylethylidene)-3, 4-dihydro-2H-benzo[b][1, 4]oxazin-2-ones (11a-n) in excellent yields (upto 97%) and (Z)-3-(2-oxo-2-phenylethylidene)-3, 4-dihydroquinoxalin-2(1H)-ones (14a-h) (upto 96% yield) are reported. The practical applicability of developed methodology were also confirmed by the gram scale synthesis of 11a, 14c and 14e; synthesis of anticancer alkaloid Cephalandole A 16 (89% yield). All the synthesized compounds 11a-n, 14a-h and 16 were assessed for their in vitro antioxidant activities in DPPH radical scavenging and FRAP assay. In DPPH assay, compounds 11a, 14c and 14e, the most active compounds of the series, were found to show IC50 value of 10.20 ± 0.08 μg/mL, 9.89 ± 0.15 μg/mL and 8.97 ± 0.13 μg/mL, respectively in comparison with standard reference (ascorbic acid, IC50 = 4.57 μg/mL). Whereas, in FRAP antioxidant assay seven compounds (11c, 11e, 11i, 11k, 11l, 14d and 14h) displayed higher antioxidant activity in comparison to the reference standard BHT (C0.5FRAP = 546.2 μM). Moreover, the cytotoxic studies of the compounds 11a, 14c, 14e and 14h were found to be non-toxic in nature in 3T3 fibroblast cell lines using MTT assay.
