57005-14-8

Usage

Uses

Used in Organic Synthesis:
(2-chloro-4-methylphenyl)thiourea is used as a reagent and intermediate in organic synthesis for various reactions.
Used in Pharmaceutical Research:
(2-chloro-4-methylphenyl)thiourea is used as a reagent and intermediate in pharmaceutical research for the development of new drugs.
Used in Agriculture:
(2-chloro-4-methylphenyl)thiourea is used as a component in the production of herbicides and pesticides due to its potential bioactive properties.
Used in Anticancer Research:
(2-chloro-4-methylphenyl)thiourea is studied for its potential anticancer activities.
Used in Antiviral Research:
(2-chloro-4-methylphenyl)thiourea is studied for its potential antiviral activities.

InChI:InChI=1/C8H9ClN2S/c1-5-2-3-7(6(9)4-5)11-8(10)12/h2-4H,1H3,(H3,10,11,12)

Upstream product

• 71233-09-5 3-benzoyl-1-(2-chloro-4-methylphenyl)-2-thiourea 
• 615-65-6 2-chloro-4-methyl-benzenamine 

Downstream Products

• 109317-46-6 2-(2-Chloro-4-methyl-phenylamino)-5,5-dimethyl-5,6-dihydro-4H-benzothiazol-7-one; hydrobromide 
• 109317-27-3 (2-Chloro-4-methyl-phenyl)-(4,5,6,7-tetrahydro-benzothiazol-2-yl)-amine 
• 52041-81-3 1-(2-Chloro-4-methyl-phenyl)-2-methyl-isothiourea; hydriodide 
• 88884-58-6 N-(2-Chloro-4-methyl-phenyl)-morpholine-4-carboxamidine; hydriodide 
• 88884-57-5 N-(2-Chloro-4-methyl-phenyl)-pyrrolidine-1-carboxamidine; hydriodide 

Relevant academic research and scientific papers

Design, synthesis and investigation on the structure-activity relationships of N-substituted 2-aminothiazole derivatives as antitubercular agents

Tuberculosis (TB) is one of the deadliest infectious diseases of all times, and its recent resurgence is a supreme matter of concern. Co-infection with HIV and, in particular, the continuous isolation of new resistant strains, makes the discovery of novel anti-TB agents a strategic priority. The research of novel agents should be driven by the accessibility of the synthetic procedure and, in particular, by the lack of cross-resistance with the drugs already marketed. Moreover, in order to shorten the duration of the therapy, and therefore decrease the rate of resistance, these molecules should be active also against the nonreplicating persistent form (NRP-TB) of the infection. The availability of an in-house small library of compounds prompted us to investigate their anti-TB activity. Two compounds, embodying a 2-aminothiazole scaffold, were found to possess a certain inhibitory activity toward Mycobacterium tuberculosis H37Rv, and therefore a medicinal chemistry campaign was initiated in order to increase the activity of the hit compounds and, especially, construct a plausible body of structure-activity relationships. The potency of the hit compound was successfully improved, and, much more importantly, some of the molecules synthesized were found to be active toward the persistent phenotype, and, also, toward a panel of resistant strains. These findings encourage further investigations around this interesting antitubercular chemotype.

Improved Procedures for the Preparation of Cycloalkyl-, Arylalkyl-, and Arylthioureas

An improved procedure for the preparation of arylthioureas consists of the reaction of benzoyl isothiocyanate with anilines in acetone and debenzoylation of the resultant N-aryl-N'-benzoylthioureas with 5percent aqueous sodium hydroxide.Bicycloalkylthioureas and N-(arylalkyl)thioureas (e.g. 9H-9-fluorenylthiourea) are directly prepared from the corresponding isothiocyanates and ammonia.

Heterocyclic derivatives of guanidine

5-Membered, 6-membered and 7-membered heterocyclic derivatives of guanidine having hypoglycemic activity.

Cardiovascular activity of aromatic guanidine compounds.

A series of aromatic guanidines and several 1-phenylbiguanides was prepared and tested for cardiovascular (CV) effects in anesthetized dogs measuring heart rate, blood pressure, carotid artery blood flow, and myocardial force changes. The predominant CV effect at minimally effective dose was vasoconstriction unassociated with cardiac stimulation. The structure-activity relationships of the compounds were discussed comparing their structural similarities to the beta-phenylethylamines. The most potent members of the series were phenylguanidines substituted in the 3 and 4 positions on the aromatic nucleus with hydroxy or chloro groups. Preliminary mechanism studies indicated that the 3,4-dihydroxyphenylguanidines act at least partially by a direct alpha-adrenergic mechanism