21521-87-9

Basic information

• Product Name: 2-CHLORO-N-(5-METHYL-1,3,4-THIADIAZOL-2-YL)ACETAMIDE
• Synonyms: 2-chloro-N-(5-methyl-1,3,4-thiadiazol-2-yl)acetamide(SALTDATA: FREE);2-(2-Chloroacetamido)-5-methyl-1,3,4-thiadiazole;2-chloro-N-(5-methyl-1,3,4-thiadiazol-2-yl)ethanamide;Acetamide, 2-chloro-N-(5-methyl-1,3,4-thiadiazol-2-yl)-
• CAS NO: 21521-87-9
• Molecular Formula: C₅H₆ClN₃OS
• Molecular Weight: 191.64
• Mol File: 21521-87-9.mol

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.519g/cm³
• Refractive Index: 1.628
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-CHLORO-N-(5-METHYL-1,3,4-THIADIAZOL-2-YL)ACETAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-N-(5-METHYL-1,3,4-THIADIAZOL-2-YL)ACETAMIDE(21521-87-9)
• EPA Substance Registry System: 2-CHLORO-N-(5-METHYL-1,3,4-THIADIAZOL-2-YL)ACETAMIDE(21521-87-9)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 21521-87-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-CHLORO-N-(5-METHYL-1,3,4-THIADIAZOL-2-YL)ACETAMIDE is used as a building block for the synthesis of biologically active molecules, contributing to the development of new drugs with antimicrobial properties. Its unique molecular structure allows for the creation of compounds that can target and combat various types of bacteria, offering potential solutions to antibiotic resistance.
Used in Agrochemical Industry:
In the agrochemical industry, 2-CHLORO-N-(5-METHYL-1,3,4-THIADIAZOL-2-YL)ACETAMIDE is used as a herbicide, helping to control and eliminate unwanted plant growth in agricultural settings. Its herbicidal properties make it a valuable tool for farmers to protect their crops and improve overall yield. Additionally, its use in agrochemicals can contribute to the development of more effective and environmentally friendly weed control solutions.

InChI:InChI=1/C5H6ClN3OS/c1-3-8-9-5(11-3)7-4(10)2-6/h2H2,1H3,(H,7,9,10)

Upstream product

• 108-33-8 5-methyl-1,3,4-thiadiazol-2-amine 
• 79-04-9 chloroacetyl chloride 

Downstream Products

• 132304-30-4 2-(dipropylaminoacetyl)amino-5-methyl-1,3,4-thiadiazole 
• 86716-28-1 2-[5-(4-Chloro-phenoxymethyl)-[1,3,4]oxadiazol-2-ylsulfanyl]-N-(5-methyl-[1,3,4]thiadiazol-2-yl)-acetamide 

Relevant articles and documents

Further insight into the dual COX-2 and 15-LOX anti-inflammatory activity of 1,3,4-thiadiazole-thiazolidinone hybrids: The contribution of the substituents at 5th positions is size dependent

Herin we report the design, synthesis, full characterization and biological investigation of new 15-LOX/COX dual inhibitors based on 1,3-thiazolidin-4-one (15-lipoxygenase pharmacophore) and 1,3,4-thiadiazole (COX pharmacophore) scaffolds. This series of molecular modifications is an extension of a previously reported series to further explore the structural activity relationship. Compounds 3a, 4e, 4n, 4q, 7 and 8 capable of inhibiting 15-LOX at (2.74, 4.2, 3.41, 10.21, 3.71 and 3.36 μM, respectively) and COX-2 at (0.32, 0.28, 0.28, 0.1, 0.28 and 0.27 μM, respectively). The results revealed that binding to 15-LOX and COX is sensitive to the bulkiness of the substituents at the 5 positions. 15-LOX bind better with small substituents, while COXs bind better with bulky substituents. Compounds 3a, 4r and 4q showed comparable in vivo anti-inflammatory activity to the reference drug (celecoxib). The ulcer liability test showed no sign of ulceration which ensures the safe gastric profile. Docking study was performed to explore the possible mode of interaction of the new compounds with the active site of human 15-LOX and COX-2. This study discloses some structural features for binding to 15-LOX and COX, thus pave the way to design anti-inflammatory agents with balanced dual inhibition of these enzymes.

Synthesis of some novel thiadiazole derivative compounds and screening their antidepressant-like activities

Novel thiadiazole derivatives were synthesized through the reaction of acetylated 2-aminothiadiazole and piperazine derivatives. The chemical structures of the compounds were clarified by Infrared Spectroscopy (IR),1H Nuclear Magnetic Resonance Spectroscopy (1H-NMR),13C Nuclear Magnetic Resonance Spectroscopy (13C-NMR) and Electronspray Ionisation Mass Spectroscopy (ESI-MS) spectroscopic methods. Antidepressant-like activities were evaluated by the tail-suspension (TST) and modified forced swimming (MFST) methods. Besides, possible influence of the test compounds on motor activities of the animals were examined by activity cage tests. In the TST, administration of the compounds 2c, 2d, 2e, 2f, 2g and 2h significantly decreased the immobility time of mice regarding the control values. Further, in the MFST, the same compounds reduced the total number of immobility behaviors while increasing swimming performance. However, no change was observed in the total number of climbing behaviors. These data suggested that compounds 2c, 2d, 2e, 2f, 2g and 2h possess notable antidepressant-like activities. Reference drug fluoxetine (10 mg/kg) was also exhibited its antidepressant activity, as expected. No significant difference was seen between the locomotor activity values of the test groups signifying that observed antidepressant-like activities are specific. Theoretical calculation of absorption, distribution, metabolism, excretion (ADME) properties for the obtained compounds were performed and obtained data supported the antidepressant-like potential of these novel thiadiazole derivatives.

Aminothiazoles as Potent and Selective Sirt2 Inhibitors: A Structure-Activity Relationship Study

Sirtuins are NAD+-dependent protein deacylases that cleave off acetyl but also other acyl groups from the ε-amino group of lysines in histones and other substrate proteins. Dysregulation of human Sirt2 (hSirt2) activity has been associated with the pathogenesis of cancer, inflammation, and neurodegeneration, which makes the modulation of hSirt2 activity a promising strategy for pharmaceutical intervention. The sirtuin rearranging ligands (SirReals) have recently been discovered by us as highly potent and isotype-selective hSirt2 inhibitors. Here, we present a well-defined structure-activity relationship study, which rationalizes the unique features of the SirReals and probes the limits of modifications on this scaffold regarding inhibitor potency. Moreover, we present a crystal structure of hSirt2 in complex with an optimized SirReal derivative that exhibits an improved in vitro activity. Lastly, we show cellular hyperacetylation of the hSirt2 targeted tubulin caused by our improved lead structure.

Acetobenzylamide piperazine derivative and application thereof as cranial nerve protective agent

The invention discloses an acetobenzylamide piperazine derivative and an application thereof as a cranial nerve protective agent. Pharmacological experiments verify that the compound disclosed by the invention shows an obvious effect against glutamic acid-induced neuron exitotoxicity in vitro and obvious anti-anoxia activity in a mouse, and a herg test further shows that the compound disclosed by the invention does not have the risk of cardiotoxicity. Therefore, the compound disclosed by the invention has the advantages of being high in activity, less in side effect and good in druggability. The compound and a medicinal preparation thereof have a good curative effect for treating cranial nerve injury diseases, for example, stroke and related diseases and do not have the risk of cardiotoxicity. The acetobenzylamide piperazine derivative is a free alkali or salt of a compound with a chemical structural formula shown in the description.

Synthesis, characterization and biological evaluation of some novel fluoroquinolones

Different derivatives of fluoroquinolones were synthesized by combining it with different thiadiazoles. The synthesized compounds were characterized by infrared spectroscopy, proton nuclear magnetic resonance and mass spectral data. The compounds were screened for their antibacterial and antifungal activity. Ciprofloxacin derivatives with thiadiazoles 7c showed good antibacterial as well as antifungal activities, whereas 13c and 13e showed antibacterial and antifungal activity respectively. Sparfloxacin derivative 8c showed both antibacterial and antifungal activity. Sparfloxacin derivatives 14b and 14e showed antibacterial and antifungal activity respectively.

Synthesis and antifungal activity of thiadiazole-functionalized chitosan derivatives

A groups of novel water soluble chitosan derivatives containing 1,3,4-thiadiazole group were synthesized including 1,3,4-thiadiazole (TPCTS), 2-methyl-1,3,4-thiadiazole (MTPCTS), and 2-phenyl-1,3,4-thiadiazole (PTPCTS). Their antifungal activity against three kinds of phytopathogens was estimated by hypha measurement in vitro, and the fungicidal assessment shows that the synthesized chitosan derivatives have excellent activity against tested fungi. Of all the synthesized chitosan derivatives, MTPCTS inhibited the growth of the tested phytopathogens most effectively with inhibitory indices of 75.3%, 82.5%, and 65.8% against Colletotrichum lagenarium (Pass) Ell.et halst, Phomopsis asparagi (Sacc.) Bubak, and Monilinia fructicola (Wint.) Honey respectively at 1.0 mg/mL. These indices are higher than those of chitosan. These data also demonstrate that the hydrophobic moiety (alkyl and phenyl) and the length of alkyl substituent in thiadiazole tend to affect the antifungal activity of chitosan derivatives. It is hypothesized that thiadiazole groups enable the synthesized chitosan to possess obviously better antifungal activity and good solubility in water.

Synthesis and biological evaluation of 2-[substituted acetyl]amino-5-alkyl-1,3,4-thiadiazoles

Some new N-substituted acetyl derivatives of 2-amino-5-alkyl-1,3,4-thiadiazoles have been prepared and investigated for antihistaminic and spasmolytic activity on guinea pig ileum. A few of the compounds showed encouraging effects. In addition, some of th

Synthesis and evaluation of substituted quinazolone derivatives for antibacterial, antifungal, and antiacetylcholinesterase activities

The synthesis of new 6-bromo- and 6,8dibromo-2-[N-(2'-alkyl -1',3',4' -thiadiazol -5' -yl)carbamoylmethylthiol] -3- aryl/cyclohexyl-4-(3H)-quinazolones is described. The synthesized derivatives were screened for antibacterial, antifungal, and antiacetylcholinesterase activities in vitro. Most of the compounds exhibited significant biological activity. The relation between their biological activity and chemical structure was studied.