Tibric acid

Tibric acid
Names
	IUPAC name 2-Chloro-5-[(3S,5R)-3,5-dimethylpiperidin-1-yl]sulfonylbenzoic acid
Identifiers
CAS Number	37087-94-8;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL2104748;
ChemSpider	29975;
ECHA InfoCard	100.048.479
EC Number	253-344-0;
KEGG	D06133;
PubChem CID	32335;
UNII	LK312SQ24Z;
CompTox Dashboard (EPA)	DTXSID1020277 ;
	InChI InChI=1S/C14H18ClNO4S/c1-9-5-10(2)8-16(7-9)21(19,20)11-3-4-13(15)12(6-11)14(17)18/h3-4,6,9-10H,5,7-8H2,1-2H3,(H,17,18)/t9-,10+ Key: IFXSWTIWFGIXQO-AOOOYVTPSA-N;
	SMILES C[C@@H]1C[C@@H](CN(C1)S(=O)(=O)C2=CC(=C(C=C2)Cl)C(=O)O)C;
Properties
Chemical formula	C14H18ClNO4S
Molar mass	331.81 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Tibric acid is a sulfamylbenzoic acid that acts as a hypolipidemic agent.[1] Although it was found to be more powerful than clofibrate in lowering lipid levels, it was found to cause liver cancer in mice and rats, and so was not introduced as a human drug.[2] In rats it causes an increase in peroxisomes, and liver enlargement, and then liver cancer. However the peroxisome changes do not occur in humans, and it is not likely to cause liver cancer in humans.[3][4]

Synthesis

Tibric acid can be made in a multi-step process. Firstly 2-chlorobenzoic acid is reacted with chlorosulfonic acid to add chlorosulfonate group in the 5- position. This reacts with 3,5-dimethylpiperidine to yield tibric acid.[5]

gollark: More than 3 million, probably.

gollark: Thanks. It's alternating between 400 and 536MH/s now.

gollark: I have no idea what that is. I just set it up to see how it worked.

gollark: I got about 54MH/s on my GTX 1050. The weird thing is that running Minecraft and the miner simultaneously only dropped the hash rate by about 1MH/s.

gollark: I have an astonishing 0.

References

Bencze, W. L.; Kritchevsky, D.; Dempsey, M. E.; Eisenberg, S.; Felts, J. M.; Frantz, I. D.; Hess, R.; Levy, R. I.; Miettinen, T. A.; Rudel, L. L.; Sodhi, H. S.; Stäubli, W.; Zemplényi, T. (2012). Hypolipidemic Agents. Springer Science & Business Media. p. 390. ISBN 9783642661907.
Lalloyer, F.; Staels, B. (14 April 2010). "Fibrates, Glitazones, and Peroxisome Proliferator-Activated Receptors". Arteriosclerosis, Thrombosis, and Vascular Biology. 30 (5): 894–899. doi:10.1161/ATVBAHA.108.179689. PMC 2997800. PMID 20393155.
Cohen, A.J.; Grasso, P. (January 1981). "Review of the hepatic response to hypolipidaemic drugs in rodents and assessment of its toxicological significance to man". Food and Cosmetics Toxicology. 19 (5): 585–605. doi:10.1016/0015-6264(81)90509-5. PMID 7030887.
Lai, David Y. (26 December 2004). "Rodent Carcinogenicity of Peroxisome Proliferators and Issues on Human Relevance". Journal of Environmental Science and Health, Part C. 22 (1): 37–55. doi:10.1081/GNC-120038005. PMID 15845221.
Lednicer, Daniel; Mitscher, Lester A.; Georg, Gunda I. (1977). The Organic Chemistry of Drug Synthesis. John Wiley & Sons. p. 87. ISBN 9780471043928.

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.

[1] Bencze, W. L.; Kritchevsky, D.; Dempsey, M. E.; Eisenberg, S.; Felts, J. M.; Frantz, I. D.; Hess, R.; Levy, R. I.; Miettinen, T. A.; Rudel, L. L.; Sodhi, H. S.; Stäubli, W.; Zemplényi, T. (2012). Hypolipidemic Agents. Springer Science & Business Media. p. 390. ISBN 9783642661907.

[2] Lalloyer, F.; Staels, B. (14 April 2010). "Fibrates, Glitazones, and Peroxisome Proliferator-Activated Receptors". Arteriosclerosis, Thrombosis, and Vascular Biology. 30 (5): 894–899. doi:10.1161/ATVBAHA.108.179689. PMC 2997800. PMID 20393155.

[3] Cohen, A.J.; Grasso, P. (January 1981). "Review of the hepatic response to hypolipidaemic drugs in rodents and assessment of its toxicological significance to man". Food and Cosmetics Toxicology. 19 (5): 585–605. doi:10.1016/0015-6264(81)90509-5. PMID 7030887.

[4] Lai, David Y. (26 December 2004). "Rodent Carcinogenicity of Peroxisome Proliferators and Issues on Human Relevance". Journal of Environmental Science and Health, Part C. 22 (1): 37–55. doi:10.1081/GNC-120038005. PMID 15845221.

[5] Lednicer, Daniel; Mitscher, Lester A.; Georg, Gunda I. (1977). The Organic Chemistry of Drug Synthesis. John Wiley & Sons. p. 87. ISBN 9780471043928.