147214-63-9

Basic information

• Product Name: cyclothialidine
• Synonyms: cyclothialidine
• CAS NO: 147214-63-9
• Molecular Formula: C₂₆H₃₅N₅O₁₂S
• Molecular Weight: 641.651
• Mol File: 147214-63-9.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 1253.4°Cat760mmHg
• Flash Point: 711.8°C
• Appearance: /
• Density: 1.6g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.684
• PKA: 3.61±0.10(Predicted)
• CAS DataBase Reference: cyclothialidine(CAS DataBase Reference)
• NIST Chemistry Reference: cyclothialidine(147214-63-9)
• EPA Substance Registry System: cyclothialidine(147214-63-9)

Safety Data

• Hazardous Substances Data: 147214-63-9(Hazardous Substances Data)

Usage

General Description

Cyclothialidine is a naturally occurring alkaloid compound that is found in a few plant species, including Cyclo-thaea hoveri. It is known for its potential as an anti-cancer agent, with some studies indicating its ability to inhibit the growth of certain cancer cell lines. Cyclothialidine has also shown anti-inflammatory properties and has been investigated for its potential in treating inflammatory conditions such as rheumatoid arthritis. Additionally, research suggests that this compound may have neuroprotective effects, making it a promising candidate for the development of new drugs for neurodegenerative diseases. However, further studies are needed to fully understand its potential applications and mechanisms of action.

InChI:InChI=1/C26H35N5O12S/c1-10-17(34)5-18(35)12-8-44-9-15(22(37)28-11(2)25(40)41)30-21(36)14(7-43-26(42)19(10)12)29-23(38)20-16(33)3-4-31(20)24(39)13(27)6-32/h5,11,13-16,20,32-35H,3-4,6-9,27H2,1-2H3,(H,28,37)(H,29,38)(H,30,36)(H,40,41)/t11-,13?,14-,15-,16+,20-/m0/s1

Upstream product

• 186132-95-6 2-benzyl 1-(tert-butyl)(2S,3R)-3-hydroxypyrrolidine-1,2-dicarboxylate 
• 186132-91-2 methyl (4R,7S)-7-({(3R)-1-[N-(tert-butoxycarbonyl)-L-seryl]-3-hydroxy-L-prolyl}amino)-12,14-bis[(tert-butyl)dimethylsilyloxy]-1,3,4,5,6,7,8,10-octahydro-11-methyl-6,10-dioxo-9,2,5-benzoxathiazacyclododecine-4-carboxylate 
• 186132-88-7 2-[(R)-2-((S)-2-tert-Butoxycarbonylamino-3-hydroxy-propionylamino)-2-methoxycarbonyl-ethylsulfanylmethyl]-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-benzoic acid 4-nitro-benzyl ester 
• 186132-89-8 (8R,11S)-11-[((2S,3R)-1-tert-Butoxycarbonyl-3-hydroxy-pyrrolidine-2-carbonyl)-amino]-2,4-bis-(tert-butyl-dimethyl-silanyloxy)-1-methyl-10,14-dioxo-5,7,8,9,10,11,12,14-octahydro-13-oxa-6-thia-9-aza-benzocyclododecene-8-carboxylic acid methyl ester 
• 186132-92-3 (8R,11S)-11-{[(2S,3R)-1-((S)-2-tert-Butoxycarbonylamino-3-hydroxy-propionyl)-3-hydroxy-pyrrolidine-2-carbonyl]-amino}-2,4-dihydroxy-1-methyl-10,14-dioxo-5,7,8,9,10,11,12,14-octahydro-13-oxa-6-thia-9-aza-benzocyclododecene-8-carboxylic acid 
• 186132-90-1 (8R,11S)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-11-[((2S,3R)-3-hydroxy-pyrrolidine-2-carbonyl)-amino]-1-methyl-10,14-dioxo-5,7,8,9,10,11,12,14-octahydro-13-oxa-6-thia-9-aza-benzocyclododecene-8-carboxylic acid methyl ester 
• 147214-64-0 2-[(R)-2-((S)-2-tert-Butoxycarbonylamino-3-hydroxy-propionylamino)-2-methoxycarbonyl-ethylsulfanylmethyl]-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-benzoic acid 
• 147214-65-1 methyl (4R,7S)-7-tert-butoxycarbonylamino-12,14-bis[(tert-butyl)dimethylsilyloxy]-1,3,4,5,6,7,8,10-octahydro-11-methyl-6,10-dioxo-9,2,5-benzoxathiaazacyclododecine-4-carboxylate 
• 147216-49-7 (8R,11S)-11-Amino-2,4-bis-(tert-butyl-dimethyl-silanyloxy)-1-methyl-10,14-dioxo-5,7,8,9,10,11,12,14-octahydro-13-oxa-6-thia-9-aza-benzocyclododecene-8-carboxylic acid methyl ester 
• 147214-70-8 4-nitrobenzyl 2-(bromomethyl)-3,5-bis[(tert-butyl)dimethylsilyloxy]-6-methylbenzoate 
• 147214-69-5 p-nitrobenzyl 3,5-bis(tert-butyldimethylsilyloxy)-2,6-dimethylbenzoate 
• 147214-68-4 4-nitrobenzyl 3,5-dihydroxy-2,6-dimethylbenzoate 
• 147214-49-1 methyl (tert-butoxycarbonyl)-L-seryl-L-cysteinate 
• 186132-86-5 3,5-Dihydroxy-2-methyl-6-piperidin-1-ylmethyl-benzoic acid 

Downstream Products

• 56-41-7 L-alanin 
• 56-45-1 L-serin 
• 52-90-4 L-Cysteine 
• 567-35-1 (2S,3R)-3-hydroxyproline 

Relevant articles and documents

184. Total synthesis of cyclothialidine

A total synthesis of cyclothialidine (1), a new DNA gyrase inhibitor isolated from Streptomyces filipinensis, is described The synthetic concept was tested by preparing the lactone 13 (Scheme 2) which contains the characteristic bicyclic core entity of 1. Key features of the synthesis of 1 are: preparation of 3,5-dihydroxy-2,6-dimethylbenzoic acid (23) from 3,5-dihydroxybenzoic acid (19) by two consecutive Mannich aminomethylation/hydrogenation sequences; benzylic N-bromosuccinimide bromination of an ester derivative 25 thereof and its subsequent coupling with Boc-Ser-Cys-OMe (11); cyclization of the ω-hydroxy acid 29 to the 12-membered lactone 30 using preferably Mitsunobu conditions; completion of the peptidic side chains of 1 using Boc strategy (Scheme 4) Optically pure cis-N-(tert-butoxycarbonyl)-3-hydroxy-L-proline ((-)-14) was obtained by resolution of the racemate via an efficient reaction sequence containing a lipase-catalyzed enantiospecific acetate hydrolysis (Scheme 3). The structure of natural 1 was confirmed by comparison with the synthetic material. The synthetic route described provides also easy access to analogues of 1, e.g., via the intermediate 30.