1234569-09-5

Basic information

• Product Name: 4-(piperidin-1-yl)-1,2,5-thiadiazol-3-yl piperidine-1-carboxylate
• CAS NO: 1234569-09-5
• Molecular Weight: 296.393
• Mol File: 1234569-09-5.mol

Chemical Properties

• CAS DataBase Reference: 4-(piperidin-1-yl)-1,2,5-thiadiazol-3-yl piperidine-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(piperidin-1-yl)-1,2,5-thiadiazol-3-yl piperidine-1-carboxylate(1234569-09-5)
• EPA Substance Registry System: 4-(piperidin-1-yl)-1,2,5-thiadiazol-3-yl piperidine-1-carboxylate(1234569-09-5)

Safety Data

• Hazardous Substances Data: 1234569-09-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-(piperidin-1-yl)-1,2,5-thiadiazol-3-yl piperidine-1-carboxylate is used as a key intermediate in the synthetic preparation of thiadiazole carbamates. These carbamates have shown potential as inhibitors of lysosomal acid lipase, an enzyme involved in the breakdown of lipids within cells. Inhibition of this enzyme is of interest for the development of therapeutics for Niemann-Pick type C disease, a rare genetic disorder characterized by the accumulation of cholesterol and other lipids in cells, leading to various health problems.
In the context of drug development, 4-(piperidin-1-yl)-1,2,5-thiadiazol-3-yl piperidine-1-carboxylate serves as a valuable building block for the creation of novel compounds with potential therapeutic applications. Its unique chemical structure allows for further modification and optimization to enhance its biological activity and selectivity, making it a promising candidate for the development of new drugs targeting lysosomal storage disorders and other related conditions.

Upstream product

• 173053-54-8 3-(piperidin-1-yl)-4-chloro-1,2,5-thiadiazole 
• 891028-86-7 3-hydroxy-4-(piperidin-1-yl)-1,2,5-thiadiazole 
• 110-89-4 piperidine 
• 13939-69-0 piperidine carbamoyl chloride 

Relevant articles and documents

MEANS AND METHODS FOR TREATING MYCOBACTERIAL DISEASES

The invention relates to compounds which are suitable for treating mycobacterial diseases and to pharmaceutical compositions containing such compounds. Also encompassed are such compounds for use in medicine. The invention further relates to a kit of parts comprising a pharmaceutical composition containing such compounds and at least one additional pharmaceutically active compound.

Human lysosomal acid lipase inhibitor lalistat impairs: Mycobacterium tuberculosis growth by targeting bacterial hydrolases

Lalistat inhibits growth of Mycobacterium tuberculosis in bacterial culture as well as in infected macrophages. Target identification by quantitative proteomics revealed a cluster of 20 hydrolytic proteins including members of the lipase family. Lipases are essential for M. tuberculosis fatty acid production and energy storage thus representing promising antibiotic targets.

Thiadiazole carbamates: Potent inhibitors of lysosomal acid lipase and potential niemann-pick type C disease therapeutics

Niemann-Pick type C (NPC) disease is a lysosomal storage disorder characterized at the cellular level by abnormal accumulation of cholesterol and other lipids in lysosomal storage organelles. Lysosomal acid lipase (LAL) has been recently identified as a potential therapeutic target for NPC. LAL can be specifically inhibited by a variety of 3,4-disubstituted thiadiazole carbamates. An efficient synthesis of the C(3) oxygenated/C(4) aminated analogues has been developed that furnishes the products in high yields and high degrees of purity. Common intermediates can also be used for the synthesis of the C(3) carbon substituted derivatives. Herein we tested various thiadiazole carbamates, amides, esters, and ketones for inhibition of LAL. In addition, we tested a diverse selection of commercially available non-thiadiazole carbamates. Our studies show that, among the compounds examined herein, only thiadiazole carbamates are effective inhibitors of LAL. We present a mechanism for LAL inhibition by these compounds whereby LAL transiently carbamoylates the enzyme similarly to previously described inhibition of acetylcholinesterase by rivastigmine and other carbamates as well as acylation of various lipases by orlistat.