16444-13-6

Basic information

• Product Name: N-(4-FORMYL-1,3-THIAZOL-2-YL)ACETAMIDE
• Synonyms: N-(4-FORMYL-1,3-THIAZOL-2-YL)ACETAMIDE;n-(4-forMylthiazol-2-yl)acetaMide;N-(4-Formyl-2-thiazolyl)acetamide
• CAS NO: 16444-13-6
• Molecular Formula: C₆H₆N₂O₂S
• Molecular Weight: 170.19
• Mol File: 16444-13-6.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• Density: 1.456±0.06 g/cm3(Predicted)
• PKA: 9.34±0.50(Predicted)
• CAS DataBase Reference: N-(4-FORMYL-1,3-THIAZOL-2-YL)ACETAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-FORMYL-1,3-THIAZOL-2-YL)ACETAMIDE(16444-13-6)
• EPA Substance Registry System: N-(4-FORMYL-1,3-THIAZOL-2-YL)ACETAMIDE(16444-13-6)

Safety Data

• Hazardous Substances Data: 16444-13-6(Hazardous Substances Data)

Usage

General Description

N-(4-Formyl-1,3-thiazol-2-yl)acetamide is a chemical compound with the formula C7H8N2O2S. It is a thiazole derivative and contains a formyl group and an acetamide group. N-(4-FORMYL-1,3-THIAZOL-2-YL)ACETAMIDE is commonly used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. It has shown potential as an antibacterial and antifungal agent in scientific studies. The chemical structure of N-(4-Formyl-1,3-thiazol-2-yl)acetamide makes it a valuable building block in organic synthesis, particularly in the development of new drugs and agricultural chemicals.

Upstream product

• 20949-80-8 N-(4-dibromomethyl-thiazol-2-yl)-acetamide 
• 20949-74-0 2-acetylamino-4-dibromomethyl-4,5-dihydro-thiazol-4-ol; hydrobromide 
• 111608-67-4 [2-(acetylamino)-1,3-thiazol-4-yl]methyl acetate 
• 51307-38-1 N-[4-(hydroxymethyl)-1,3-thiazol-2-yl]acetamide 
• 7460-59-5 N-(4-(chloromethyl)thiazol-2-yl)acetamide 

Downstream Products

• 16443-89-3 4-(2-acetylamino-thiazol-4-ylmethylene)-2-phenyl-4H-oxazol-5-one 
• 16443-97-3 2-acetylamino-5-bromo-thiazole-4-carbaldehyde 
• 737823-38-0 methyl 4-[(Z)-2-(2-acetamido-1,3-thiazol-4-yl)vinyl]benzoate 
• 874900-74-0 N-{4-[(Z)-2-(2,3-dinitrophenyl)vinyl]-1,3-thiazol-2-yl}acetamide 
• 874899-97-5 {4-[2-(2-acetamido-1,3-thiazol-4-yl)ethyl]phenyl}acetic acid 
• 737827-27-9 N-{4-[2-(Z)-(3,4-dinitrophenyl)vinyl]-1,3-thiazol-2-yl}acetamide 
• 1442469-22-8 tert-butyl (4-{4-[2-(2-acetamido-1,3-thiazol-4-yl)ethyl]benzyl}-1H-imidazol-2-yl)carbamate 
• 1442469-21-7 tert-butyl (4-{4-[2-(2-acetamido-1,3-thiazol-4-yl)ethyl]phenyl}-1H-imidazol-2-yl)carbamate 
• 1030892-96-6 4-[2-(2-acetamido-1,3-thiazol-4-yl)ethyl]benzoic acid 
• 737823-39-1 methyl 4-[2-(2-acetamido-1,3-thiazol-4-yl)ethyl]benzoate 
• 737823-06-2 N-{4-[(Z)-2-(4-cyanophenyl)ethenyl]-1,3-thiazol-2-yl}acetamide 
• 737822-88-7 N-{4-[(Z)-2-(4-nitrophenyl)ethenyl]-1,3-thiazol-2-yl}acetamide 
• 1030893-59-4 3-{2-[2-(acetylamino)-1,3-thiazol-4-yl]vinyl}phenylacetic acid 

Relevant articles and documents

Synthesis and SAR study of new thiazole derivatives as vascular adhesion protein-1 (VAP-1) inhibitors for the treatment of diabetic macular edema

Vascular adhesion protein-1 (VAP-1), an amine oxidase that is also known as a semicarbazide-sensitive amine oxidase (SSAO), is present in particularly high levels in human plasma, and is considered a potential therapeutic target for various inflammatory diseases, including diabetes complications such as macular edema. In our VAP-1 inhibitor program, structural modifications following high-throughput screening (HTS) of our compound library resulted in the discovery that thiazole derivative 10, which includes a guanidine group, shows potent human VAP-1 inhibitory activity (IC50 of 230 nM; rat IC 50 of 14 nM). Moreover, compound 10 exhibited significant inhibitory effects on ocular permeability in STZ-induced diabetic rats.

THIAZOLE DERIVATIVES HAVING VAP-1 INHIBITORY ACTIVITY

A compound of the formula (I): U-V-W-X-Y-Z (I) wherein U is lower alkyl; V is -CONH- or -NR1CO- wherein R1 is a hydrogen or lower alkyl; W is a bond or lower alkylene; X is a bivalent residue derived from optionally substituted thiazole; Y is a bond or lower alkylene; and Z is a group of the formula: or wherein R2 is a group of the formula: -A-B-D-E-F-G wherein A is a bond or lower alkylene; B is a bond, -NH- or ; D is a bond, -CS- or -CO-; E is a bond or -NH-; F is a bond, -CO-, -O- or -SO2-; and G is lower alkyl, optionally protected amino, -OH, phenyl, or ; and R3 is lower alkyl, provided that when Z is a group of the formula: , then G should not be amino, when Z is a group of the formula: , then G should not be , when Z is a group of the formula: and G is optionally protected amino, then D should be -CS-, or then A should be lower alkylene, B or E should be -NH- and F should be -CO-; or a pharmaceutically acceptable salt thereof useful as a vascular adhesion protein-1 (VAP-1) inhibitor as well as a pharmaceutical composition and a method for preventing or treating a VAP-1 associated disease, especially macular edema, which method includes administering an effective amount of the compound or a pharmaceutically acceptable salt thereof to a subject, and the like.

Synthesis and pharmacological properties of N-[4-[4-(1H-indol-3- yl)piperidinoalkyl]-2-thiazolyl]alkanesulfonamides as novel antiallergic agents

A number of N-[4-[4-(1H-indol-3-yl)piperidinoalkyl]-2- thiazolyl]alkanesulfonamides (8-21) were synthesized and evaluated for their preventive effects on systemic anaphylaxis in guinea pigs. Structure-activity analysis revealed that methane- and ethanesulfonamide derivatives having a one to three methylene tether between the piperidine and thiazole rings exhibited potent activity but the introduction of a substituent on the indole part reduced the activity. Administration (100 mg/kg p.o.) of the four compounds 8, 9, 12, 13, together with ketotifen, oxatomide, terfenadine and azelastine as reference compounds, to mice revealed that only compound 8 caused no significant increase of the sleeping time induced by hexobarbital. In addition, compound 8 (10 mg/kg i.v.) did not change the electroencephalogram in conscious rabbits. These results led to the selection of N-[4-[4-(1H-indol-3-yl)piperidinomethyl]-2-thiazolyl]methanesulfonamide (8, FK613) for further development as a novel antiallergic agent. Clinical evaluation of FK613 is now in progress.