Synthesis of curacin A, an antimitotic cyclopropane-thiazoline from the marine cyanobacterium Lyngbya majuscula

Lai, Jing Yu; Yu, Jurong; Mekonnen, Belew; Falck, John R.

doi:10.1016/0040-4039(96)01616-4

Cited by 60 publications

(23 citation statements)

References 16 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Curacin is an unusual acetogenin entailing a thiazoline ring. It shows strong toxicity towards L1210 leukaemic cell lines and inhibits tubulin polymerization by binding at colchicine site (Lai et al, 1996).…”

Section: Cyanobacteria As a Producer Of Bioactive Compoundsmentioning

confidence: 99%

Bioactive Compounds from Cyanobacteria and Microalgae: An Overview

Singh

Kate

Banerjee

2005

Critical Reviews in Biotechnology

524

262

View full text Add to dashboard Cite

Cyanobacteria (blue-green algae) are photosynthetic prokaryotes used as food by humans. They have also been recognized as an excellent source of vitamins and proteins and as such are found in health food stores throughout the world. They are also reported to be a source of fine chemicals, renewable fuel and bioactive compounds. This potential is being realized as data from research in the areas of the physiology and chemistry of these organisms are gathered and the knowledge of cyanobacterial genetics and genetic engineering increased. Their role as antiviral, anti-tumour, antibacterial, anti-HIV and a food additive have been well established. The production of cyanobacteria in artificial and natural environments has been fully exploited. In this review the use of cyanobacteria and microalgae, production processes and biosynthesis of pigments, colorants and certain bioactive compounds are discussed in detail. The genetic manipulation of cyanobacteria and microalgae to improve their quality are also described at length.

show abstract

Section: Cyanobacteria As a Producer Of Bioactive Compoundsmentioning

confidence: 99%

Bioactive Compounds from Cyanobacteria and Microalgae: An Overview

Singh

Kate

Banerjee

2005

Critical Reviews in Biotechnology

524

262

View full text Add to dashboard Cite

show abstract

“…anticancer, anti-HIV, pheromone activity and cell division inhibition, [11][12][13][14][15][16] while small molecular mass thiazolines have found applications in food and flavor industries. 17 However, it's surprising that thiazolines have not been much explored in the field of tubercular activity though they are found to be good antibiotics.…”

Section: Figure-2mentioning

confidence: 99%

A facile synthesis and evaluation of new biomolecule-based coumarin–thiazoline hybrids as potent anti-tubercular agents with cytotoxicity, DNA cleavage and X-ray studies

et al. 2015

View full text Add to dashboard Cite

An efficient and rapid synthesis of coumarin-thiazoline hybrids (1a-1j) under microwave irradiation has been described in high yields. The synthesized compounds (1a-1l) were characterized by elemental and spectroscopic analysis; in addition, the structures of compound (1a), (1b), (1e) and (1h) have been elucidated by single crystal X-ray diffraction technique. All the newly synthesized compounds were screened for their in-vitro anti-tubercular activity and DNA cleavage study, while the most active compounds were subjected for their cytotoxic assay on Vero cell lines. Among the tested, compound (1b) exhibited excellent anti-tubercular activity MIC 0.09 µg/mL with low level of cytotoxicity, suggesting that compound (1b) is a promising lead for subsequent investigation in search of new anti-tubercular agents. Further, DNA cleavage study by agarose gel electrophoresis method revealed that compounds (1b), (1d), (1f) and (1i) cleaved DNA more efficiently and thereby exhibits nuclease activity.This research paper is dedicated to my beloved Prof. M. V. Kulkarni on his 60 th birthday.From the results, it's clear that none of the compounds violate the rule and they fall well in the range as stated by RO5 to qualify as a drug candidate.Coumarins are an elite class of oxygen-containing fused heterocycles, which are widely distributed in nature, especially in plants. They form a large class of important lactones with a fused structure of benzene and α-pyrone ring, and virtually contain π -π conjugated system with rich electron and good charge transport properties. Moreover, the unique structure of coumarin has a special ability which allows its derivatives readily interact with a diversity of enzymes and receptors in organisms through weak bond interactions and thereby exhibit wide potentiality as medicinal drugs. Hence, coumarin based compounds have attracted special interest in the area of medicinal chemistry and their outstanding contributions in the prevention and treatment of numerous diseases have become an extremely attractive highlight. 4 Recently many coumarin scaffolds have been investigated as potential candidates for the treatment of tuberculosis for e.g., Diaryl coumarin (1), 4 aryl/alkyl sulfonyl methyl coumarin (2), Iodinated-4-aryloxymethylcoumarin (3) and Chalconated coumarin (4) have been reported, to exhibit potent anti-tubercular activity with MICs of 0.24, 0.78, 1.56 and 3.5µg/ml respectively, 5 whereas naturally occurring coumarins such as Ferulenol (5), Suberosin (6), Osthol (7), Scopoletin (8) and Umbelliferone (9) exhibited MICs of 2, 16, 32, 42 and 58.3 µg/ml respectively. 6 Reports have also suggested that coumarin class compounds targets the fatty acyl-ACP synthetase activity of the FadD32 enzyme 5a,6a which is essential for Mtb survival as it plays a critical role in the biosynthesis of the unique branched fatty acids (mycolic acids) that make up the Mtb cell wall. Hence looking into the biological significance of coumarin, particularly in the field of tuberculosis, we anticipate that coumarin cou...

show abstract

“…For example, the thiazolium ring present in vitamin B 1 serves as an electron sink, and its coenzyme form is important for the decarboxylation of α-keto-acids (7). Especially noteworthy is the observation that some thiazolines show interesting anti-HIV or anticancer activities and can inhibit cell division (8)(9)(10). In view of the importance of thiazoles and their derivatives, several methods for their syntheses have been developed.…”

Section: Introductionmentioning

confidence: 99%

Solvent-free synthesis of 1-[3-alkyl-4-methyl-2-thioxo-2,3-dihydrothiazole-5-yl]-ethanones in a multicomponent reaction

Iravani

Karami

Asadimoghaddam

et al. 2012

Journal of Sulfur Chemistry

View full text Add to dashboard Cite

A simple and efficient one-pot synthesis of 1-[3-alkyl-4-methyl-2-thioxo-2,3-dihydrothiazole-5-yl]-ethanones from the reaction of primary alkylamines and carbon disulfide in the presence of 3-chloro acetylacetone is described. This protocol has several advantages such as lack of need for a solvent and catalyst, high yields, mild conditions and short reaction times. R N H 2 H 3 C O O CH 3 Cl + r.t. , 2-4 hr CS 2 solvent-free N S S R CH 3 O CH 3

show abstract

Synthesis of curacin A, an antimitotic cyclopropane-thiazoline from the marine cyanobacterium Lyngbya majuscula

Cited by 60 publications

References 16 publications

Bioactive Compounds from Cyanobacteria and Microalgae: An Overview

Bioactive Compounds from Cyanobacteria and Microalgae: An Overview

A facile synthesis and evaluation of new biomolecule-based coumarin–thiazoline hybrids as potent anti-tubercular agents with cytotoxicity, DNA cleavage and X-ray studies

Solvent-free synthesis of 1-[3-alkyl-4-methyl-2-thioxo-2,3-dihydrothiazole-5-yl]-ethanones in a multicomponent reaction

Contact Info

Product

Resources

About