45964-97-4

Usage

Uses

Used in Pharmaceutical Industry:
N-(4-CHLORO-PHENYL)-GUANIDINE is used as a reagent for the synthesis of pyrimidine derivatives, which act as hSMG-1 inhibitors. These inhibitors are potential targets for cancer treatment, making N-(4-CHLORO-PHENYL)-GUANIDINE a valuable component in the development of novel anticancer drugs.
Used in Antibacterial Applications:
N-(4-CHLORO-PHENYL)-GUANIDINE can also be utilized as a new antibacterial agent, contributing to the discovery and creation of innovative solutions for combating bacterial infections and addressing the growing issue of antibiotic resistance.

Upstream product

• 15150-25-1 N-cyanobenzamide 
• 20265-96-7 p-chloroaniline hydrochloride 
• 13463-94-0 N-(4-chlorophenyl)cyanamide 
• 106-47-8 4-chloro-aniline 
• 420-04-2 CYANAMID 

Downstream Products

• 539-03-7 N-(4-chlorophenyl)acetamide 
• 140-38-5 N-(4-chlorophenyl)urea 
• 5429-13-0 N-(4-chloro-phenyl)-N'-(4-methyl-6-oxo-1,6-dihydro-pyrimidin-2-yl)-guanidine 
• 855954-07-3 N-(4-chloro-phenyl)-N'-(6-methyl-2-oxo-1,2-dihydro-pyrimidin-4-yl)-guanidine 
• 500-92-5 proguanil 
• 6712-59-0 5-(4-chloro-phenyl)-1-isopropyl-1-methyl-biguanide 
• 5442-06-8 1,1-diethyl-5-(4-chloro-phenyl)-biguanide 
• 102474-46-4 (4-chloro-phenylcarbamimidoyl)-amidophosphoric acid dibenzyl ester 
• 60221-93-4 N¹-p-Chlorphenyl-N⁵-ethylbiguanid 
• 13463-94-0 N-(4-chlorophenyl)cyanamide 
• 106-47-8 4-chloro-aniline 
• 87215-95-0 5,5-diethyl-2-(4-chloro-anilino)-1H-pyrimidine-4,6-dione 
• 109810-06-2 (4-chloro-phenylcarbamimidoyl)-amidophosphoric acid diphenyl ester 
• 56858-82-3 N-(4-chloro-phenylcarbamimidoyl)-N'-isopropyl-urea 

Relevant academic research and scientific papers

Synthesis and SAR of 4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline derivatives as potent and selective CDK4/6 inhibitors

CDK4/6 pathway is an attractive target for development of anti-cancer drugs. Herein, we reported the design and synthesis of a series of 4,5-dihydro-1H-pyrazolo [4,3-h]quinazoline derivatives as selective CDK4/6 inhibitors. Applied with the optimizing strategy to the initial scaffold, it is found that compound 13n is able to selectively inhibit CDK4 and CDK6 with IC50 values 0.01 and 0.026 μM, respectively. The compound showed good anti-proliferative activity when tested in a panel of tumor cell lines with CDK4/6 related mechanism of action, the results clearly suggest that compound 13n works much better than Ly2385219 which is a selective CDK4/6 inhibitor. This compound was also found to have favorable pharmacokinetic parameters. Taken together, compound 13n could be selected for further preclinical evaluation.

Reaction of quinones and guanidine derivatives: Simple access to bis-2-aminobenzimidazole moiety of benzosceptrin and other benzazole motifs

A new strategy for the synthesis of 2-aminobenzimidazol-6-ols via a reaction of quinones with guanidine derivatives is reported. Sequential application of this methodology provided a simple access to the first benzosceptrin analogue bearing a bis-2-aminoimidazole moiety. A concomitant addition of two guanidines to the naphtho[1′,2′:4,5]imidazo[1,2-a] pyrimidine-5,6-dione, which includes the redox neutral debenzylation and guanidine-assisted cleavage of the 2-aminopyrimidine part resulted in the synthesis of the free challenging contiguous bis-2-aminoimidazole moiety of benzosceprins in one step.

Design and synthesis of a novel series of N,4-diphenylpyrimidin-2-amine derivatives as potent and selective PI3Kγ inhibitors

Due to the increasing evidence linking the PI3Kγ pathway to various disease states, PI3Kγ is becoming an important target for cancer treatment. Herein we designed and synthesized a novel series of N,4-diphenylpyrimidin-2-amine derivatives with low CDOCKER-INTERACTION-ENERGY and then evaluated their PI3Kγ in vitro inhibitory activities and in vitro antiproliferation assays against four human cancer cells. Among the compounds we synthesized, compound C8 (IC50 = 65 nM) demonstrated the most potent inhibitory activity against PI3Kγ kinase as well as at the cellular level, compared to the control drug TG100713 (IC50 = 127 nM). Moreover, molecular docking analysis was also performed to determine possible binding modes between PI3Kγ and the target compounds.

Identification of pyrimidine derivatives as hSMG-1 inhibitors

hSMG-1 kinase plays a dual role in a highly conserved RNA surveillance pathway termed nonsense-mediated RNA decay (NMD) and in cellular genotoxic stress response. Since deregulation of cellular responses to stress contributes to tumor growth and resistance to chemotherapy, hSMG-1 is a potential target for cancer treatment. From our screening efforts, we have identified pyrimidine derivatives as hSMG-1 kinase inhibitors. We report structure-based optimization of this pan-kinase scaffold to improve its biochemical profile and overall kinome selectivity, including mTOR and CDK, to generate the first reported selective hSMG-1 tool compound.

Palladium-catalyzed C-H functionalization using guanidine as a directing group: Ortho arylation and olefination of arylguanidines

Palladium-catalyzed C-H functionalization using guanidine as the directing group was achieved under mild reaction conditions. Various guanidine derivatives were produced in moderate to good yields by using simple unactivated arenes or ethyl acrylate as the source of arylation or olefination, respectively.