186132-85-4

Upstream product

• 110-89-4 piperidine 
• 50-00-0 formaldehyd 
• 99-10-5 3,5-Dihydroxybenzoic acid 

Downstream Products

• 4780-63-6 3,5-dihydroxy-2-methylbenzoic acid 
• 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 
• 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 
• 147214-70-8 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 
• 186132-86-5 3,5-Dihydroxy-2-methyl-6-piperidin-1-ylmethyl-benzoic acid 
• 147214-67-3 3,5-dihydroxy-2,6-dimethylbenzoic acid 
• 147214-63-9 cyclothialidine 

Relevant academic research and scientific papers

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.

ROMATIC COMPOUNDS AND PHARMACEUTICAL USES THEREOF

The present disclosure relates to compounds of the general formula (I): wherein R1, R2, R3, R4, R5, R6, and R7 may be chosen from different substituents; n is 0, 1, or 2; and X is a hydroxymethyl or a carboxylic acid or a derivative thereof, such as a carboxylate, such as a carboxylic ester, a glyceride, an anhydride, a phospholipid, a carboxamide, a phospholipid, or a prodrug thereof; or a pharmaceutically acceptable salt, solvate, solvate of such salt or a prodrug thereof. The present disclosure also relates to pharmaceutical compositions and lipid compositions comprising at least one compound according to the present disclosure, and to such compounds for use as medicaments or for use in therapy, in particular for the treatment of diseases related to metabolic diseases and liver diseases, such as non-alcoholic fatty liver disease and cholestasis diseases.