173053-54-8

Basic information

• Product Name: 1-(4-CHLORO-[1,2,5]THIADIAZOL-3-YL)-PIPERIDINE
• Synonyms: 1-(4-CHLORO-[1,2,5]THIADIAZOL-3-YL)-PIPERIDINE;AKOS BB-9731;1-(4-chloro-1,2,5-thiadiazol-3-yl)piperidine(SALTDATA: FREE);3-Chloro-4-(piperidin-1-yl)-1,2,5-thiadiazole
• CAS NO: 173053-54-8
• Molecular Formula: C7H10ClN3S
• Molecular Weight: 203.69
• Mol File: 173053-54-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-(4-CHLORO-[1,2,5]THIADIAZOL-3-YL)-PIPERIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-CHLORO-[1,2,5]THIADIAZOL-3-YL)-PIPERIDINE(173053-54-8)
• EPA Substance Registry System: 1-(4-CHLORO-[1,2,5]THIADIAZOL-3-YL)-PIPERIDINE(173053-54-8)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 173053-54-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-(4-CHLORO-[1,2,5]THIADIAZOL-3-YL)-PIPERIDINE is used as a compound for the development of pharmaceuticals targeting neurological disorders. Its unique structure suggests that it may interact with receptor sites in the central nervous system, offering potential therapeutic benefits for patients suffering from such conditions.
Additionally, due to its potential activity at receptor sites, 1-(4-CHLORO-[1,2,5]THIADIAZOL-3-YL)-PIPERIDINE may also be utilized in the development of other pharmaceuticals for various conditions, depending on further research and development in the industry.

Upstream product

• 110-89-4 piperidine 
• 5728-20-1 3,4-dichloro-1,2,5-thiadiazole 
• 871918-91-1 piperidineglyoxime 

Downstream Products

• 501104-16-1 4-(piperidin-1-yl)-1,2,5-thiadiazol-3-yl morpholine-4-carboxylate 
• 1234569-09-5 4-(piperidin-1-yl)-1,2,5-thiadiazol-3-yl piperidine-1-carboxylate 
• 891028-86-7 3-hydroxy-4-(piperidin-1-yl)-1,2,5-thiadiazole 

Relevant articles and documents

Synthesis of 4-substituted 3-chloro-1,2,5-thiadiazoles from monosubstituted glyoximes

One-pot synthesis of 3-chloro-1,2,5-thiadiazoles from monosubstituted glyoximes and sulfur monochloride was developed.

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.

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.

Novel methods and compounds employed therein

Preparation of an optically active alkamine in the sinister configuration, or a derivative of said alkamine, which is reacted with an 3-X-4-chloro(or RO-- where R is hydrogen or an alkali metal)-1,2,5-thiadiazole to prepare S-3-X-4-(3-substituted amino-2-hydroxypropoxy)-1,2,5-thiadiazole beta adrenergic blocking agents. Novel 3-morpholino-4-chloro(or RO--)-1,2,5-thiadiazoles and their preparation also are described.