19563-04-3

Usage

Uses

Used in Chemical Synthesis:
4-CHLORO-BENZAMIDINE is used as a reagent in chemical synthesis for its ability to facilitate the production of pharmaceuticals and agrochemicals. Its unique properties make it a key component in creating a variety of compounds.
Used in Research:
In the field of biochemistry and molecular biology, 4-CHLORO-BENZAMIDINE serves as a research tool, aiding scientists in their studies and experiments due to its reactivity and structural characteristics.
Used in Pharmaceutical Development:
4-CHLORO-BENZAMIDINE is used as an intermediate in the synthesis of other organic compounds, which are essential in developing new pharmaceuticals with potential therapeutic applications.
Used in Antimicrobial and Antiparasitic Drug Development:
4-CHLORO-BENZAMIDINE is studied for its potential antimicrobial and antiparasitic activities, making it a subject of interest for the development of new drugs to combat various infections and diseases.
Used in Agrochemical Production:
In the agrochemical industry, 4-CHLORO-BENZAMIDINE is utilized in the synthesis of compounds that help in the development of pesticides and other agricultural chemicals, contributing to crop protection and yield enhancement.

Upstream product

• 14401-51-5 4-chlorobenzamidine hydrochloride 
• 5033-28-3 4-chlorobenzamidoxime 
• 5033-28-3 4-chloro-N-hydroxybenzimidamide 
• 40546-41-6 ethyl-4-chlorobenzimidate hydrochloride 
• 623-03-0 4-Cyanochlorobenzene 
• 98-10-2 benzenesulfonamide 
• 74-11-3 para-chlorobenzoic acid 
• 631-61-8 ammonium acetate 

Downstream Products

• 30362-65-3 bis-(4-chloro-phenyl)-trichloromethyl-[1,3,5]triazine 
• 21036-90-8 4-benzofuran-2-yl-2-(4-chloro-phenyl)-1⁽³⁾H-imidazole 
• 886761-28-0 4-amino-2-(p-chlorophenyl)-5-cyano-6-(p-nitrophenyl)pyrimidine 
• 886761-30-4 4-amino-2-(p-chlorophenyl)-5-cyano-6-(m-nitrophenyl)pyrimidine 
• 83217-77-0 2-p-chlorophenyl-4,6-dihydroxypyrimidine 
• 950486-12-1 C₂₁H₁₇ClN₄O₂S 
• 950485-84-4 C₂₀H₁₅ClN₄OS 
• 43089-48-1 2-(4-chlorophenyl)pyrido[2,3-d]pyrimidin-4-one 
• 1613435-87-2 2-(4-chlorophenyl)pyrido[4,3-d]pyrimidin-4-one 
• 14945-95-0 4-amino-6-(4-chlorophenyl)-2-methylthio-1,3,5-triazine 
• 95675-06-2 N,N,N'-tris<(4-chlorophenyl)thio>-4-chlorobenzenecarboximidamide 
• 95675-04-0 N,N,N'-tris(phenylthio)-4-chlorobenzenecarboximidamide 
• 35371-53-0 2-(4-chloro-phenyl)-4-(3-methyl-benzo[b]thiophen-2-yl)-1H-imidazole 
• 21036-75-9 2-(4-chloro-phenyl)-4-thiophen-2-yl-1⁽³⁾H-imidazole 

Relevant academic research and scientific papers

Novel Allosteric Inhibitors of Deoxyhypusine Synthase against Malignant Melanoma: Design, Synthesis, and Biological Evaluation

Based on the novel allosteric site of deoxyhypusine synthase (DHPS), two series of 30 novel 5-(2-methoxyphenoxy)-2-phenylpyrimidin-4-amine derivatives as DHPS inhibitors were designed and synthesized. Among them, compound8m, with the best DHPS inhibitory potency (IC50= 0.014 μM), exhibited excellent inhibition against melanoma cells, which was superior to that of GC7. Besides, molecular docking and molecular dynamics (MD) simulations further proved that compound8mwas tightly bound to the allosteric site of DHPS. Flow cytometric analysis and enzyme-linked immunosorbent assay (ELISA) showed that compound8mcould inhibit the intracellular reactive oxygen species (ROS) level. Furthermore, by western blot analysis, compound8meffectively activated caspase 3 and decreased the expressions of GP-100, tyrosinase, eIF5A2, MMP2, and MMP9. Moreover, both Transwell analysis and wound healing analysis showed that compound8mcould inhibit the invasion and migration of melanoma cells. In thein vivostudy, the tumor xenograft model showed that compound8meffectively inhibited melanoma development with low toxicity.

Silver-catalyzed [3+2+1] annulation of aryl amidines with benzyl isocyanide

A silver-catalyzed [3+2+1] annulation of amidines with benzyl isocyanide toward 2,4-diaryl-1,3,5-triazines was developed. A variety of symmetrical and unsymmetrical products were obtained in moderate to good yields. This work also features an oxidant-free approach to 2,4-disubstituted triazines.

Preparation technique of dabigatran methanesulfonate

The invention discloses a preparation technique of dabigatran methanesulfonate. The technique comprises the following steps: 1) by using a compound I and glycine as raw materials, carrying out condensation and salification to obtain a compound II; 2) by using p-halobenzonitrile (III) as a raw material, synthesizing p-halobenzamidine (IV) under the actions of a catalyst and an aminating agent, and carrying out condensation on the p-halobenzamidine (IV) and n-hexyl chloroacetate to obtain a compound V; and 3) carrying out condensation and salification on the compound V and the compound II to obtain the dabigatran methanesulfonate. The synthesis method has the advantages of mild reaction conditions for each step and high selectivity, and is simple to operate. The dabigatran methanesulfonate has high yield and purity. The technique has the advantages of less discharge of three wastes and environment friendliness, does not need column chromatography purification, and is suitable for industrial production.

Electrochemical and mARC-catalyzed enzymatic reduction of para-substituted benzamidoximes: Consequences for the prodrug concept "amidoximes instead of amidines"

The mitochondrial amidoxime reducing component (mARC) activates amidoxime prodrugs by reduction to the corresponding amidine drugs. This study analyzes relationships between the chemical structure of the prodrug and its metabolic activation and compares its enzyme-mediated vs. electrochemical reduction. The enzyme kinetic parameters KM and Vmax for the N-reduction of ten para-substituted derivatives of the model compound benzamidoxime were determined by incubation with recombinant proteins and subcellular fractions from pig liver followed by quantification of the metabolites by HPLC. A clear influence of the substituents at position 4 on the chemical properties of the amidoxime function was confirmed by correlation analyses of 1H NMR chemical shifts and the redox potentials of the 4-substituted benzamidoximes with Hammett's σ. However, no clear relationship between the kinetic parameters for the enzymatic reduction and Hammett's σ or the lipophilicity could be found. It is thus concluded that these properties as well as the redox potential of the amidoxime can be largely ignored during the development of new amidoxime prodrugs, at least regarding prodrug activation.

TANKYRASE INHIBITORS

The present invention relates to a compound of formula I wherein X is C(R6) or N, Y is C or N, and ring A, ring B, R1 and R2 have the meanings defined herein, provided that when ring B is carbocyclic, X is C(R6); or a pharmaceutically acceptable salt or solvate thereof. The compounds are tankyrase-1 and tankyrase-2 inhibitors and are useful in the treatment of a number of conditions, including cancer.

Degradation of MAC13243 and studies of the interaction of resulting thiourea compounds with the lipoprotein targeting chaperone LolA

The discovery of novel small molecules that function as antibacterial agents or cellular probes of biology is hindered by our limited understanding of bacterial physiology and our ability to assign mechanism of action. We previously employed a chemical genomic strategy to identify a novel small molecule, MAC13243, as a likely inhibitor of the bacterial lipoprotein targeting chaperone, LolA. Here, we report on the degradation of MAC13243 into the active species, S-(4-chlorobenzyl)isothiourea. Analogs of this compound (e.g., A22) have previously been characterized as inhibitors of the bacterial actin-like protein, MreB. Herein, we demonstrate that the antibacterial activity of MAC13243 and the thiourea compounds are similar; these activities are suppressed or sensitized in response to increases or decreases of LolA copy number, respectively. We provide STD NMR data which confirms a physical interaction between LolA and the thiourea degradation product of MAC13243, with a K d of ～150 μM. Taken together, we conclude that the thiourea series of compounds share a similar cellular mechanism that includes interaction with LolA in addition to the well-characterized target MreB.

Unsymmetrical 1α3-1,2,4,6-thiatriazinyls with aryl and trifluoromethyl substituents: Synthesis, crystal structures, EPR spectroscopy, and voltammetry

A general synthetic route to 3-trifluoromethyl-5-aryl-1α3- 1,2,4,6-thiatriazinyl radicals was developed. X-ray structures were obtained for all five neutral radicals and show that they exist in the solid state as cofacial dimers linked by S...S contacts. X-ray structures were also obtained for two of the precursor chlorothiatriazines along with several aryl N-imidoylamidines, p-methoxybenzamidine, and N-chlorosulfonyl- N,N'-benzamidine. Cyclic voltammetric studies were performed on the [R2C 2N3S]. radicals in CH3CN and CH 2Cl2 with [nBu4N][PF6] as the supporting electrolyte under vacuum conditions in an all-glass electrochemical cell. The results provide quasi-reversible formal potentials for the [R2C2N3S]-/0 process in the range of -0.61 to -0.47 V, irreversible peak potentials for the [R2C 2N3S]0/+ process from 0.59 to 0.91 V at lower concentrations, and the appearance of a second, reversible oxidation process from 0.69 to 0.94 V at higher concentrations (versus the Fc0/+ couple; Fc = ferrocene). This behavior was indicative of monomer-dimer equilibrium in solution, as ascertained from digital models of the voltammograms. There is a small but measurable trend in both the oxidation and reduction potentials with varying remote aryl substituents. EPR spectra were obtained for all five neutral radicals in CH2Cl2 solutions, which confirm the concentration of the unpaired electron density on the heterocyclic core. Trends were also seen in the hyperfine splitting constants aN with varying remote aryl substituents. Calculations were performed for all three oxidation states of the [R2C2N3S]-/./+ monomeric rings; the resulting theoretical redox energies correlate well with solution phase voltammetric data.

Pyridine and pyrimidine derivatives

The present invention provides compounds of formula (I) wherein R1, R2, R3, R4 and X are as defined in the specification, and pharmaceutically acceptable salts thereof. The compounds are useful for the treatment

4-Amino-2-substituted-5-pyrimidinecarboxamidoximes and carbothioamides

4-Amino-2-substituted-5-pyrimidinecarboxamidoximes and carbothioamides are immunomodulatory agents useful in the treatment of immune system diseases and disorders.