70390-94-2

Basic information

• Product Name: 2-(chloroMethyl)-5-phenyl-1,3,4-thiadiazole
• Synonyms: 2-(chloroMethyl)-5-phenyl-1,3,4-thiadiazole;2-(chloroMethyl)-5-phenyl-1
• CAS NO: 70390-94-2
• Molecular Formula: C₉H₇ClN₂S
• Molecular Weight: 210.68328
• Mol File: 70390-94-2.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-(chloroMethyl)-5-phenyl-1,3,4-thiadiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(chloroMethyl)-5-phenyl-1,3,4-thiadiazole(70390-94-2)
• EPA Substance Registry System: 2-(chloroMethyl)-5-phenyl-1,3,4-thiadiazole(70390-94-2)

Safety Data

• Hazardous Substances Data: 70390-94-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-(chloroMethyl)-5-phenyl-1,3,4-thiadiazole is used as an antifungal and antimicrobial agent for its potential to combat a range of pathogens.
Used in Chemical Synthesis:
2-(chloroMethyl)-5-phenyl-1,3,4-thiadiazole is used as a building block for the synthesis of new pharmaceutical compounds, contributing to the development of innovative treatments and therapies.
Used in Agriculture:
2-(chloroMethyl)-5-phenyl-1,3,4-thiadiazole is used as a potential agent for controlling fungal and microbial infections in crops, thereby enhancing crop yield and quality.
Used in Materials Science:
2-(chloroMethyl)-5-phenyl-1,3,4-thiadiazole is used in the development of new materials with specific properties, such as antimicrobial coatings or components for various applications.

Upstream product

• 33575-83-6 2-(chloromethyl)-5-phenyl-1,3,4-oxadiazole 
• 50677-24-2 Ν-p-methylbenzoyl-N'-chloroacetyl 
• 36743-66-5 ethyl chloroacetimidate hydrochloride 
• 20605-40-7 thiobenzhydrazide 

Downstream Products

• 70390-98-6 N-hydroxy-5-phenyl-[1,3,4]thiadiazole-2-carboximidoyl chloride 
• 104090-56-4 Methyl-(5-phenyl-[1,3,4]thiadiazol-2-ylmethyl)-amine 
• 1293956-51-0 2-(bis((5-phenyl-1,3,4-thiadiazol-2-yl)methylthio)methylene)malononitrile 
• 121564-79-2 2-Azidomethyl-5-phenyl-[1,3,4]thiadiazole 
• 1342816-82-3 2-cyanoethyl [(5-phenyl-1 ,3,4-thiadiazol-2-yl)methyl]dithiocarbamate 
• 85730-57-0 C-(5-Phenyl-[1,3,4]thiadiazol-2-yl)-methylamine 
• 1287305-28-5 5-(bis((5-phenyl-1,3,4-thiadiazol-2-yl)methylthio)methylene)-dihydro-2-thioxopyrimidine-4,6-(1H,5H)-dione 
• 1287305-25-2 5-(bis((5-phenyl-1,3,4-thiadiazol-2-yl)methylthio)methylene)pyrimidine-2,4,6-(1H,3H,5H)-trione 
• 70391-04-7 N-hydroxy-5-phenyl-[1,3,4]thiadiazole-2-carboximidoyl azide 
• 70391-08-1 2-phenyl-1,3,4-thiadiazole-5-carbonitrile 

Relevant articles and documents

Discovery of 3,5-dimethylisoxazole derivatives as novel, potent inhibitors for bromodomain and extraterminal domain (BET) family

Bromodomain and extra-terminal (BET) is a promising therapeutic target for various hematologic cancers. We used the BRD4 inhibitor compound 13 as a lead compound to develop a variety of compounds, and we introduced diverse groups into the position of the compound 13 orienting toward the ZA channel. A series of compounds (14–23, 38–41, 43, 47–49) bearing triazolopyridazine motif exhibited remarkable BRD4 protein inhibitory activities. Among them, compound 39 inhibited BRD4(BD1) protein with an IC50 of 0.003 μM was superior to lead compound 13. Meanwhile, compound 39 possess activity, IC50 = 2.1 μM, in antiproliferation activity against U266 cancer cells. On the other hand, compound 39 could arrest tumor cells into the G0/G1 phase and induce apoptosis, which was consistent with its results in inhibiting cell proliferation. Biological and biochemical data suggest that BRD4 protein might be a therapeutic target and that compound 39 is an excellent lead compound for further development.

Discovery of first-in-class thiazole-based dual FFA1/PPARδ agonists as potential anti-diabetic agents

The free fatty acid receptor 1 (FFA1 or GPR40) and peroxisome proliferator-activated receptor δ (PPARδ) have attracted a lot of attention due to their role in promoting insulin secretion and sensibility, respectively, which are two major features of diabetes. Therefore, the dual FFA1/PPARδ agonists would increase insulin secretion and sensibility by FFA1 and PPARδ activation. In this study, we hybrid FFA1 agonist AM-4668 with PPARδ agonist GW501516, leading to the identification of orally bioavailable dual agonist 32, which revealed high selectivity over other PPARs. Moreover, compound 32 exhibited good pharmacokinetic profiles with high plasma concentration, sustained half-life and low clearance in vivo. During the hypoglycemic test, a dual agonist 32 enhanced the tolerance of ob/ob mice for glucose loading in a dose-dependent manner. Our results suggest that dual FFA1/PPARδ agonist could be a valuable therapy for type 2 diabetes.

Biphenyl heterocyclic derivatives, their preparation and their use as medicaments (by machine translation)

The present invention relates to a novel biphenyl heterocyclic derivative represented by a general formula (I) and a preparation method thereof and use of a pharmaceutical composition containing the derivative for preparation of a drug for treating diabetes. The biphenyl heterocyclic derivative has extremely excellent hypoglycemic activity in vivo, and excellent in vivo safety and low liver toxicity risk of the compound having such a structure are unexpectedly found, and the novel biphenyl heterocyclic derivative may be used for preventing or treating diabetes.

Design, synthesis and Structure-activity relationship studies of new thiazole-based free fatty acid receptor 1 agonists for the treatment of type 2 diabetes

The free fatty acid receptor 1 (FFA1/GPR40) has attracted interest as a novel target for the treatment of type 2 diabetes. Several series of FFA1 agonists including TAK-875, the most advanced compound terminated in phase III studies due to concerns about liver toxicity, have been hampered by relatively high molecular weight and lipophilicity. Aiming to develop potent FFA1 agonists with low risk of liver toxicity by decreasing the lipophilicity, the middle phenyl of TAK-875 was replaced by 11 polar five-membered heteroaromatics. Subsequently, systematic exploration of SAR and application of molecular modeling, leads to the identification of compound 44, which was an excellent FFA1 agonist with robustly hypoglycemic effect both in normal and type 2 diabetic mice, low risks of hypoglycemia and liver toxicity even at the twice molar dose of TAK-875. Meanwhile, two important findings were noted. First, the methyl group in our thiazole series occupied a small hydrophobic subpocket which had no interactions with TAK-875. Furthermore, the agonistic activity revealed a good correlation with the dihedral angle between thiazole core and the terminal benzene ring. These results promote the understanding of ligand-binding pocket and might help to design more promising FFA1 agonists.

Discovery of novel heteroarylmethylcarbamodithioates as potent anticancer agents: Synthesis, structure-activity relationship analysis and biological evaluation

A series of new analogs based on the structure of lead compound 10 were designed, synthesized and evaluated for their in vitro anti-cancer activities against four selected human cancer cell lines (HL-60, Bel-7402, SK-BR-3 and MDA-MB-468). Several synthesized compounds exhibited improved anti-cancer activities comparing with lead compound 10. Among them, 1,3,4-oxadiazole analogs 17o showed highest bioactivity with IC50 values of 1.23, 0.58 and 4.29 μM against Bel-7402, SK-BR-3 and MDA-MB-468 cells, respectively. It is noteworthy that 17o has potent anti-proliferation activity toward a panel of cancer cells with relatively less cytotoxicity to nonmalignant cells. The further mechanistic study showed that it induced apoptosis and cell cycle arrest through disrupting spindle assembly in mitotic progression, indicating these synthesized dithiocarbamates represented a novel series of anti-cancer compounds targeting mitosis.

Synthesis and biological activity of 2-(bis((1,3,4-oxadiazolyl/1,3,4- thiadiazolyl)methylthio)methylene)malononitriles

The reactivity of ketene dithiolates in the presence of different equivalents of sodium ethoxide was studied. 2-(Bis((5-aryl-1,3,4-oxadiazol-2-yl) methylthio)methylene)malononitriles 5 and 2-(bis((5-aryl-1,3,4-thiadiazol-2-yl) methylthio)methylene)malononitriles 6 were prepared by the reaction of malononitrile with carbon disulfide and 5-aryl-2-(chloromethyl)-1,3,4- oxadiazoles 3/5-aryl-2-(chloromethyl)-1,3,4-thiadiazoles 4. The preliminary antimicrobial and antioxidant activities of the lead compounds were assayed.

One-pot synthesis of 5-{[Bis(azolylmethylthio)]methylene}pyrimidine-2,4,6- (1H,3H,5H)-triones

A new class of hitherto unknown trisheterocycles, bisoxadiazolyl/ bisthiadiazolyl pyrimidinetriones/thioxopyrimidinediones was prepared in a one-pot reaction and their antimicrobial activity was studied.

Syntheses, antifeedant activity, and QSAR analysis of new Oxa(thia)diazolyl 3(2H)-pyridazinones

Twenty-eight new oxa(thia)diazolyl 3(2H)-pyridazinone derivatives were synthesized. Some compounds showed good chronic growth activities against the armyworm, Pseudaletia separata (Walker). Their EC50 values were determined in vivo. Nineteen 2-