22067-26-1

Basic information

• Product Name: 1-(4-phenylthiazol-2-yl)-2-(propan-2-ylidene)hydrazine
• Synonyms: 1-(4-phenylthiazol-2-yl)-2-(propan-2-ylidene)hydrazine
• CAS NO: 22067-26-1
• Molecular Weight: 231.321
• Mol File: 22067-26-1.mol

Chemical Properties

• CAS DataBase Reference: 1-(4-phenylthiazol-2-yl)-2-(propan-2-ylidene)hydrazine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-phenylthiazol-2-yl)-2-(propan-2-ylidene)hydrazine(22067-26-1)
• EPA Substance Registry System: 1-(4-phenylthiazol-2-yl)-2-(propan-2-ylidene)hydrazine(22067-26-1)

Safety Data

• Hazardous Substances Data: 22067-26-1(Hazardous Substances Data)

Usage

Chemical structure

1-(4-phenylthiazol-2-yl)-2-(propan-2-ylidene)hydrazine is a chemical compound that features a thiazole ring and a hydrazine group.

Building block

It is commonly used as a building block in the synthesis of various pharmaceuticals and organic compounds.

Biological activities

Due to its structural features, it has the potential to exhibit various biological activities.

Drug development

It is known for its use in the development of new drugs.

Precursor

It serves as a precursor in the synthesis of heterocyclic compounds.

Anti-inflammatory properties

It has been studied for its potential anti-inflammatory properties.

Antimicrobial properties

It has been investigated for its potential antimicrobial properties.

Antifungal properties

It has been researched for its potential antifungal properties.

Importance in medicinal chemistry

Due to its potential applications and properties, 1-(4-phenylthiazol-2-yl)-2-(propan-2-ylidene)hydrazine is considered an important chemical in the field of medicinal chemistry.

Upstream product

• 67-64-1 acetone 
• 98-86-2 acetophenone 
• 70-11-1 α-bromoacetophenone 
• 1752-30-3 Acetone thiosemicarbazone 

Downstream Products

• 1609483-09-1 ethyl 1-(4-phenylthiazol-2-yl)-4,5-dihydro-1H-benzo[g]indazole-3-carboxylate 
• 1566598-87-5 ethyl 4,5-diphenyl-1-(4-phenylthiazol-2-yl)-1H-pyrazole-3-carboxylate 
• 1609483-08-0 ethyl 4-ethyl-5-phenyl-1-(4-phenylthiazol-2-yl)-1H-pyrazole-3-carboxylate 
• 1609483-07-9 ethyl 5-(2,4-dichlorophenyl)-4-methyl-1-(4-phenylthiazol-2-yl)-1H-pyrazole-3-carboxylate 
• 1609483-06-8 ethyl 5-(4-chlorophenyl)-4-methyl-1-(4-phenylthiazol-2-yl)-1H-pyrazole-3-carboxylate 
• 1609483-05-7 ethyl 4-methyl-5-phenyl-1-(4-phenylthiazol-2-yl)-1H-pyrazole-3-carboxylate 
• 1609483-04-6 ethyl 5-(2,4-dichlorophenyl)-1-(4-phenylthiazol-2-yl)-1H-pyrazole-3-carboxylate 
• 1609483-03-5 ethyl 5-(4-chlorophenyl)-1-(4-phenylthiazol-2-yl)-1H-pyrazole-3-carboxylate 
• 34176-52-8 2-hydrazino-4-phenylthiazole 
• 1609483-02-4 ethyl 5-phenyl-1-(4-phenylthiazol-2-yl)-1H-pyrazole-3-carboxylate 

Relevant articles and documents

Structure-based design of potent human dihydroorotate dehydrogenase inhibitors as anticancer agents

It has been proven that inhibiting human dihydroorotate dehydrogenase (hDHODH) restricts the growth of rapidly proliferating cells, thus hDHODH can be developed as a promising target for the treatment of immunological disease and cancer. Here, a succession of substituted hydrazino-thiazole derivatives were designed, synthesized, and biologically evaluated through structure-based optimization, of which compound 22 was the most potent inhibitor of hDHODH with an IC50 value of 1.8 nM. Furthermore, 22 exhibited much better antiproliferative activity than brequinar, both in HCT-116 and BxPC-3 cancer cell lines. Flow cytometry analysis revealed that 22 induced S phase cell cycle arrest and promoted induction of apoptosis. All results established a proof that blocking the pyrimidine de novo synthesis pathway by inhibiting the rate-limiting enzyme hDHODH is an attractive therapy for cancer.

Microwave and ultrasound-assisted synthesis of thiosemicarbazones and their corresponding (4,5-substituted-thiazol-2-yl)hydrazines

Hantzsch cyclization of thiosemicarbazone intermediates is a very popular approach to the synthesis of substituted thiazoles. We developed a convenient microwave and ultrasound-assisted method both for the synthesis of 1-(alkyliden/cycloalkyliden/aryliden)thiosemicarbazone intermediates and their cyclization into (4,5-substituted-thiazol-2-yl)hydrazines. The search for optimal reaction conditions included the use of different catalysts (Lewis acids and resins) and solvents at discrete temperatures, pressures, and irradiation powers. Comparing yields, reaction times, and efforts proved that microwave and ultrasound-assisted techniques outmatch conventional heating and have a remarkable influence on the synthesis.

An efficient one-pot synthesis of aryl-substituted 1-(thiazol-2-yl)-1H- pyrazole-3-carboxylates via a hantzsch synthesis-knorr reaction sequence

The treatment of α-bromoalkyl aryl ketones and 2-(propan-2-ylidene) hydrazine carbothioamide afforded 4-aryl-2-(2-(propan-2-ylidene)hydrazinyl) thiazoles via a Hantzsch-thiazole synthesis, which reacted with 4-aryl-2,4-diketoesters via a sequential Knorr-

Evaluation of a large library of (thiazol-2-yl)hydrazones and analogues as histone acetyltransferase inhibitors: Enzyme and cellular studies

Recently we described some (thiazol-2-yl)hydrazones as antiprotozoal, antifungal and anti-MAO agents as well as Gcn5 HAT inhibitors. Among these last compounds, CPTH2 and CPTH6 showed HAT inhibition in cells and broad anticancer properties. With the aim to identify HAT inhibitors more potent than the two prototypes, we synthesized several new (thiazol-2-yl)hydrazones including some related thiazolidines and pyrimidin-4(3H)-ones, and we tested the whole library existing in our lab against human p300 and PCAF HAT enzymes. Some compounds (1x, 1c', 1d', 1i' and 2m) were more efficient than CPTH2 and CPTH6 in inhibiting the p300 HAT enzyme. When tested in human leukemia U937 and colon carcinoma HCT116 cells (100 μM, 30 h), 1x, 1i' and 2m gave higher (U937 cells) or similar (HCT116 cells) apoptosis than CPTH6, and were more potent than CPTH6 in inducing cytodifferentiation (U937 cells).

Maillard reaction inhibitor

A compound represented by the following formula is disclosed: STR1 wherein the all symbols are defined in the disclosure. A process for producing the compound, and a method for treating diseases caused by a Maillard reaction in living body using the compo