2009
DOI: 10.4149/neo_2009_04_321
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The design, synthesis and anticancer activity of new nitrogen mustard derivatives of natural indole phytoalexin 1-methoxyspirobrassinol

Abstract: Nitrogen mustards cis- 1-methoxy-2-deoxy-2-[N,N-bis(2´-chloroethyl)amino]spirobrassinol (4) and trans-1-methoxy-2-deoxy-2-[N,N-bis(2´-chloroethyl)amino]spirobrassinol (5) derived from 1-methoxyspirobrassinol, an indole phytoalexin produced by the Japanese radish Raphanus sativus var. hortensis were designed as prospective dual-action compounds with DNA-alkylating effect and glutathione-depleting effects that may sensitize cancer cells to alkylating agents. Both new compounds demonstrated cytostatic/cytotoxic e… Show more

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Cited by 15 publications
(8 citation statements)
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“…Resveratrol presents some anticancer activities in hepatoma, lung carcinoma and intestinal tumors ([14] and references therein). However lack of efficacy of natural phytoalexins in reducing tumors has led to a number of investigations regarding the design and synthesis of more potent anticancer derivatives of known phytoalexins such as brassinin [121], methoxybrassinol [122] and resveratrol [123].…”
Section: Role Of Phytoalexins In Human Healthmentioning
confidence: 99%
“…Resveratrol presents some anticancer activities in hepatoma, lung carcinoma and intestinal tumors ([14] and references therein). However lack of efficacy of natural phytoalexins in reducing tumors has led to a number of investigations regarding the design and synthesis of more potent anticancer derivatives of known phytoalexins such as brassinin [121], methoxybrassinol [122] and resveratrol [123].…”
Section: Role Of Phytoalexins In Human Healthmentioning
confidence: 99%
“…Phytoalexins are secondary metabolites produced by certain plants in response to pathogen attack or various forms of stress. Indole phytoalexins from cruciferous plants, such as brassinin, spirobrassinin, 1-methoxyspirobrassinol and camalexin demonstrate in vivo cytostatic/cytotoxic effects against cultured human solid tumour and leukemia cell lines [9,10]. Synthetic 2-amino analogs of 1-methoxyspirobrassinol were found to be significantly cytotoxic against human cancer cell lines (Fig.…”
Section: Introductionmentioning
confidence: 97%
“…Indoles and its biheterocycles are featured in a wide variety of biological and pharmacologically active compounds [3]. The indole derivatives are known to possess anticancer [4,5], antioxidant [6,7], anti-inflammatory [8,9], antiviral [10], and antihypertensive [11] activities.…”
Section: Introductionmentioning
confidence: 99%