4022-81-5

Basic information

• Product Name: 1-(4-CHLOROPHENYL)BIGUANIDE HYDROCHLORIDE
• Synonyms: 1-(p-chlorophenyl)biguanidehydrochloride;1-(p-chlorophenyl)-biguanidmonohydrochloride;n-(4-chlorophenyl)-imidocarbonimidicdiamidemonohydrochloride;BUTTPARK 45\01-24;([(4-CHLOROANILINO)(IMINO)METHYL]AMINO)METHANIMIDAMIDE HYDROCHLORIDE;1-(4-CHLOROPHENYL)BIGUANIDE HYDROCHLORIDE;1-(4-CHLOROPHENYL)BIGUANIDE HYDROCHLOR&;1-(4-Chlorophenyl)biguanideHCl
• CAS NO: 4022-81-5
• Molecular Formula: C₈H₁₀ClN₅*ClH
• Molecular Weight: 248.11
• EINECS: 226-155-6
• Product Categories: Guanidines;Nitrogen Compounds;Organic Building Blocks;Building Blocks;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks
• Mol File: 4022-81-5.mol
• Article Data: 6

Chemical Properties

• Melting Point: 239-242 °C(lit.)
• Boiling Point: 426.4 °C at 760 mmHg
• Flash Point: 211.7 °C
• Appearance: /
• Vapor Pressure: 1.78E-07mmHg at 25°C
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• Sensitive: Hygroscopic
• Stability: Hygroscopic
• BRN: 3732533
• CAS DataBase Reference: 1-(4-CHLOROPHENYL)BIGUANIDE HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-CHLOROPHENYL)BIGUANIDE HYDROCHLORIDE(4022-81-5)
• EPA Substance Registry System: 1-(4-CHLOROPHENYL)BIGUANIDE HYDROCHLORIDE(4022-81-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: DU1780200
• HazardClass: IRRITANT
• Hazardous Substances Data: 4022-81-5(Hazardous Substances Data)

Usage

Description

1-(4-CHLOROPHENYL)BIGUANIDE HYDROCHLORIDE is a chemical compound belonging to the class of biguanides. It is characterized by the presence of a 4-chlorophenyl group attached to the biguanide structure. 1-(4-CHLOROPHENYL)BIGUANIDE HYDROCHLORIDE exhibits significant biological activity, particularly as an inhibitor of dihydrofolate reductase (DHFR), which plays a crucial role in cellular metabolism and DNA synthesis.

Uses

1. Used in Pharmaceutical Applications:
1-(4-CHLOROPHENYL)BIGUANIDE HYDROCHLORIDE is used as an inhibitor for dihydrofolate reductase (DHFR) due to its ability to significantly inhibit the enzyme. This inhibition can potentially lead to the disruption of cellular metabolism and DNA synthesis, making it a promising candidate for the development of therapeutic agents targeting various diseases, particularly those involving rapid cell proliferation.
2. Used in Anticancer Research:
In the field of oncology, 1-(4-CHLOROPHENYL)BIGUANIDE HYDROCHLORIDE is used as a research tool to study the role of dihydrofolate reductase (DHFR) in cancer cell growth and proliferation. By understanding the compound's interaction with DHFR, researchers can gain insights into the development of novel anticancer drugs that target this enzyme, potentially leading to more effective treatments for various types of cancer.
3. Used in Drug Design and Development:
1-(4-CHLOROPHENYL)BIGUANIDE HYDROCHLORIDE serves as a valuable starting point for the design and development of new drugs targeting dihydrofolate reductase (DHFR). Its structure can be modified and optimized to improve its potency, selectivity, and pharmacokinetic properties, ultimately leading to the creation of more effective therapeutic agents for the treatment of diseases associated with dysregulated DHFR activity.
4. Used in Biochemical and Molecular Biology Research:
In addition to its pharmaceutical applications, 1-(4-CHLOROPHENYL)BIGUANIDE HYDROCHLORIDE is also used as a research tool in biochemical and molecular biology studies. It can be employed to investigate the structure, function, and regulation of dihydrofolate reductase (DHFR) and its role in various biological processes, including cell growth, DNA replication, and gene expression.

InChI:InChI=1/C8H10ClN5/c9-5-1-3-6(4-2-5)13-8(12)14-7(10)11/h1-4H,(H6,10,11,12,13,14)/p+2

Upstream product

• 106-47-8 4-chloro-aniline 
• 127099-85-8 N-Cyanoguanidine 

Downstream Products

• 645-18-1 N-(4-chloro-phenyl)-6-methyl-[1,3,5]triazine-2,4-diamine 
• 30355-61-4 6-(chloromethyl)-N²-(4-chlorophenyl)-1,3,5-triazine-2,4-diamine 
• 1269527-19-6 N₂-(4-chlorophenyl)-6-((5-methyl-1H-benzo[d]imidazol-2-ylthio)methyl)-1,3,5-triazine-2,4-diamine 
• 1269527-14-1 6-[(1H-benzo[d]imidazol-2-ylthio)methyl]-N₂-(4-chlorophenyl)-1,3,5-triazine-2,4-diamine 
• 5405-65-2 N₂-(4-chloro-phenyl)-6,6-dimethyl-1,6-dihydro-1,3,5-triazine-2,4-diamine 
• 102557-50-6 1-(4-chloro-phenyl)-6-methyl-6-(2-morpholin-4-yl-ethyl)-1,6-dihydro-[1,3,5]triazine-2,4-diamine 
• 102003-56-5 1-(4-chloro-phenyl)-6-methyl-6-morpholin-4-ylmethyl-1,6-dihydro-[1,3,5]triazine-2,4-diamine 
• 16018-51-2 4,6-Dimethyl-2-(p-chlorphenyl)-guanidinopyrimidin 
• 104509-37-7 1-(4-chloro-phenyl)-6-ethyl-6-methyl-1,6-dihydro-[1,3,5]triazine-2,4-diamine 
• 516-21-2 cycloguanil 
• 30805-25-5 1-(4-chloro-phenyl)-6-isopropyl-1,6-dihydro-[1,3,5]triazine-2,4-diyldiamine 
• 131762-02-2 1-(4-chloro-phenyl)-6-methyl-6-propyl-1,6-dihydro-[1,3,5]triazine-2,4-diyldiamine; hydrochloride 
• 5429-13-0 N-(4-chloro-phenyl)-N'-(4-methyl-6-oxo-1,6-dihydro-pyrimidin-2-yl)-guanidine 
• 50427-07-1 1-[4-amino-6-(4-chloro-anilino)-[1,3,5]triazin-2-yl]-propan-2-one 

Relevant articles and documents

Identifying Lysophosphatidic Acid Acyltransferase β (LPAAT-β) as the Target of a Nanomolar Angiogenesis Inhibitor from a Phenotypic Screen Using the Polypharmacology Browser PPB2

By screening a focused library of kinase inhibitor analogues in a phenotypic co-culture assay for angiogenesis inhibition, we identified an aminotriazine that acts as a cytostatic nanomolar inhibitor. However, this aminotriazine was found to be completely inactive in a whole-kinome profiling assay. To decipher its mechanism of action, we used the online target prediction tool PPB2 (http://ppb2.gdb.tools), which suggested lysophosphatidic acid acyltransferase β (LPAAT-β) as a possible target for this aminotriazine as well as several analogues identified by structure–activity relationship profiling. LPAAT-β inhibition (IC50 ≈15 nm) was confirmed in a biochemical assay and by its effects on cell proliferation in comparison with a known LPAAT-β inhibitor. These experiments illustrate the value of target-prediction tools to guide target identification for phenotypic screening hits and significantly expand the rather limited pharmacology of LPAAT-β inhibitors.

BIGUANIDE COMPOUND AND USE THEREOF

The present invention relates to a guanidine compound and a use thereof, and more specifically, to a guanidine derivative showing excellent effects of inhibiting cancer cell proliferation, cancer metastasis, and cancer recurrence; a preparation method thereof; and a pharmaceutical composition containing the same as an active ingredient. Compared to existing drugs, the guanidine derivative according to the present invention shows excellent effects of inhibiting cancer cell proliferation, cancer metastasis, and cancer recurrence even with small doses, and may thus be effectively used in preventing or treating various cancers such as uterine cancer, breast cancer, stomach cancer, brain cancer, rectal cancer, colorectal cancer, lung cancer, skin cancer, blood cancer, liver cancer, etc., inhibiting cancer cell proliferation and cancer metastasis.

High yielding microwave-assisted synthesis of 2-(arylmethyl)amino-4-arylamino-6-alkyl-1,3,5-triazines

An efficient and practical procedure was developed to prepare novel 2-(arylmethyl)amino-4-arylamino-6-alkyl-1,3,5-triazines, starting from dicyandiamide and the corresponding arylamines under microwave irradiation and its scope is demonstrated with a number of examples. The valuable feature of this procedure included the short reaction times, high yields, and easy operation.