501104-16-1

Basic information

• Product Name: 4-(piperidin-1-yl)-1,2,5-thiadiazol-3-yl morpholine-4-carboxylate
• CAS NO: 501104-16-1
• Molecular Weight: 298.366
• Mol File: 501104-16-1.mol

Chemical Properties

• CAS DataBase Reference: 4-(piperidin-1-yl)-1,2,5-thiadiazol-3-yl morpholine-4-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(piperidin-1-yl)-1,2,5-thiadiazol-3-yl morpholine-4-carboxylate(501104-16-1)
• EPA Substance Registry System: 4-(piperidin-1-yl)-1,2,5-thiadiazol-3-yl morpholine-4-carboxylate(501104-16-1)

Safety Data

• Hazardous Substances Data: 501104-16-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-(piperidin-1-yl)-1,2,5-thiadiazol-3-yl morpholine-4-carboxylate is used as a synthetic intermediate for the development 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 treatment of Niemann-Pick type C disease, a rare genetic disorder characterized by the accumulation of cholesterol and other lipids in cells, leading to various health complications.
In the context of Niemann-Pick type C disease therapeutics, 4-(piperidin-1-yl)-1,2,5-thiadiazol-3-yl morpholine-4-carboxylate serves as a key building block in the synthesis of novel thiadiazole carbamate derivatives. These derivatives are being investigated for their ability to modulate lysosomal acid lipase activity, potentially offering a new approach to managing the symptoms and progression of Niemann-Pick type C disease.
Furthermore, the unique structural features of 4-(piperidin-1-yl)-1,2,5-thiadiazol-3-yl morpholine-4-carboxylate may also render it suitable for exploration in other therapeutic areas, such as the development of new drugs targeting various diseases and conditions. Its potential applications in the pharmaceutical industry are diverse and warrant further research and development to fully understand its capabilities and limitations.

Upstream product

• 15159-40-7 4-morpholinocarbonyl chloride 
• 891028-86-7 3-hydroxy-4-(piperidin-1-yl)-1,2,5-thiadiazole 
• 110-89-4 piperidine 
• 173053-54-8 3-(piperidin-1-yl)-4-chloro-1,2,5-thiadiazole 

Relevant articles and documents

Optimization of 1,2,5-thiadiazole carbamates as potent and selective ABHD6 inhibitors

At present, inhibitors of α/β-hydrolase domain 6 (ABHD6) are viewed as a promising approach to treat inflammation and metabolic disorders. This article describes the development of 1,2,5-thiadiazole carbamates as ABHD6 inhibitors. Altogether, 34 compounds were synthesized, and their inhibitory activity was tested using lysates of HEK293 cells transiently expressing human ABHD6 (hABHD6). Among the compound series, 4-morpholino-1,2,5-thiadiazol-3-yl cyclooctyl(methyl)carbamate (JZP-430) potently and irreversibly inhibited hABHD6 (IC50 = 44 nM) and showed ～ 230-fold selectivity over fatty acid amide hydrolase (FAAH) and lysosomal acid lipase (LAL), the main off-targets of related compounds. Additionally, activity-based protein profiling indicated that JZP-430 displays good selectivity among the serine hydrolases of the mouse brain membrane proteome. JZP-430 has been identified as a highly selective, irreversible inhibitor of hABHD6, which may provide a novel approach in the treatment of obesity and type II diabetes.

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.