Synthesis of curacin A, an antimitotic cyclopropane-thiazoline from the marine cyanobacterium Lyngbya majuscula
Charette cyclopropanation, thioamide to thiazoline conversion, and Mitsunobu dehydrative alkylation with phenylsulfonylacetonitrile were exploited for a versatile, stereocontrolled synthesis of the title lipid.
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Anticancer potential of natural peptides from terrestrial and marine environments: A review
2021, Phytochemistry LettersPt(II) and Pd(II) complexes with a thiazoline derivative ligand: Synthesis, structural characterization, antiproliferative activity and evaluation of pro-apoptotic ability in tumor cell lines HT-29 and U-937
2020, Journal of Inorganic BiochemistryCitation Excerpt :Also, synthetic oligomers derived from 2-thiazoline have been synthesized and inhibit cell growth in pancreatic, prostate and colonic cancer [24]. Furthermore, it is known that some synthetic derivatives containing the 2-thiazoline ring exhibit antitumor activity [25,26]. Additionally, Onen-Bayram et al. [27] found a new compound designed based on a thiazolidine ring that trigger caspase-9 dependent apoptosis in liver cancer cells and Romagnoli et al. [28] have observed that novel hybrid molecules containing 5-benzylidene thiazolidine-2,4-dione induce apoptosis in U-937 cells.
Exploration of aroyl/heteroaroyl iminothiazolines featuring 2,4,5-trichlorophenyl moiety as a new class of potent, selective, and in vitro efficacious glucosidase inhibitors
2017, Bioorganic ChemistryCitation Excerpt :Several α-glucosidase inhibitors like acarbose, voglibose, and miglitol, have appeared in clinic for the treatment of type II diabetes mellitus [7,8], however, number and intensity of side effects invite the scientific community to develop potent, structurally diverse, safe and efficacious drugs for the effective treatment of diabetes mellitus. 2-Imino-1,3-thiazoline or thiazol-2-imine core is among the highly recognized families of heterocyclic compounds due to its widespread existence in several drug scaffolds displaying a plethora of biological activities such as anti-inflammatory, analgesic, antihypertensive [9], antimicrobial [10,11] antiallergic [12], anti HIV [13], anti-cancer [14], antimitotic [15,16], anti-urease [17], kinase (CDK1, CDK5, and GSK3) inhibition [18], and melanin reducing activities [19]. Several natural products such as curacin A [20], thiangazole [21], mirabazoles [22], and apratoxins [23] possess thiazoline moiety and this significant prevalence triggers the use of thiazolines as readily exploitable building blocks in pharmaceutical drug discovery [24,25].
Copper(II) halide coordination complexes with 2-(3,5-diphenyl-1-pyrazolyl)-2-thiazoline (DPhPyTn): Synthesis, characterization and crystal structures
2015, PolyhedronCitation Excerpt :In the other hand, the thiazoline ring is present in many biologically active products, including natural [8] and synthetic products. Some thiazoline-containing compounds exhibit anti HIV-1, antimitotic, and fungicidal activities, and have recently found applications as building blocks in pharmaceutical drug discovery [9–11]. Our group has been and is interested in the interaction between pyrazole/thiazoline ligands and transition metal ions [12–15].
Novel bioactive peptides from cyanobacteria: Functional, biochemical, and biomedical significance
2012, Studies in Natural Products ChemistryCitation Excerpt :Curacin A exhibits potent antiproliferative and cytotoxic activity against colon, renal, and breast-cancer derived cell lines [67]. It also shows strong toxicity toward L1210 leukemic cell lines and inhibits tubulin polymerization by binding at the colchicine site [7]. Further, the oxime analogue was much less lipophilic with only slightly weak human tumor cell growth potential.