Cycloguanil hydrochloride

Base Information

• Chemical Name: Cycloguanil hydrochloride
• CAS No.: 152-53-4
• Molecular Formula: C11H14 Cl N5 . Cl H
• Molecular Weight: 288.18
• European Community (EC) Number: 624-607-0
• NSC Number: 3074
• UNII: 5C8E0L7498
• DSSTox Substance ID: DTXSID7049053
• Wikidata: Q27148906
• ChEMBL ID: CHEMBL544227
• Mol file: 152-53-4.mol

Synonyms:1,3,5-triazine-2,4-diamine, 1-(4-chlorophenyl)-1,6-dihydro-6,6-dimethyl-, hydrochloride (1:1);1-(4-chlorophenyl)-1,6-dihydro-6,6-dimethyl-1,2,5-triazine-2,4-diamine;1-(4-chlorophenyl)-1,6-dihydro-6,6-dimethyl-1,3,5-triazine-2,4-diamine monohydrochloride;BN-24-10;BN2410;chlorcycloguanil;chloroguanide triazine hydrochloride;cycloguanil;cycloguanil hydrochloride;cycloquanil

Chemical Property of Cycloguanil hydrochloride

Chemical Property:

• Vapor Pressure: 1.25E-06mmHg at 25°C
• Melting Point: 210-2150C
• Boiling Point: 400.7°Cat760mmHg
• Flash Point: 196.1°C
• PSA: 80.00000
• Density: g/cm³
• LogP: 2.66430
• Storage Temp.: -20?C Freezer
• Solubility.: DMSO (Slightly, Sonicated), Methanol (Slightly), Water (Slightly)
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 287.0704509
• Heavy Atom Count: 18
• Complexity: 355

Purity/Quality:

99% ^*data from raw suppliers

Cycloguanil-d4 Hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1(N=C(N=C(N1C2=CC=C(C=C2)Cl)N)N)C.Cl
• Description: Cycloguanil is the active metabolite of the antimalarial prodrug proguanil. Cycloguanil is formed from proguanil by the cytochrome P450 (CYP) isoforms CYP2C19 and CYP3A in human liver microsomes. It is an inhibitor of dihydrofolate reductase (DHFR; Kis = 1.5 and 0.79 nM for the P. falciparum and P. berghei enzymes, respectively). It is active against ten P. falciparum field isolates (IC50s = 0.12-1,400 μg/ml). Cycloguanil reduces parasitemia in a mouse model of P. berghei infection (ED50 = 2 mg/kg). It also reduces parasitemia in a rhesus monkey model of P. cynomolgi infection when administered at a dose of 0.3 mg/kg.
• Uses: Labelled antimalarial drug Antimalarial drug.

Technology Process of Cycloguanil hydrochloride

There total 3 articles about Cycloguanil hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 69.0%

1-(4-chlorophenyl)biguanide hydrochloride (4022-81-5,55307-40-9) + acetone (67-64-1) → cycloguanil hydrochloride (152-53-4)

Guidance literature:

With hydrogenchloride; Triethyl orthoacetate; In methanol; at 20 ℃;

DOI:10.1081/SCC-120005415

Reference yield: 62.0%

4-chloro-aniline (106-47-8) + N-Cyanoguanidine (127099-85-8,780722-26-1,461-58-5) + acetone (67-64-1) → cycloguanil hydrochloride (152-53-4)

Guidance literature:

With hydrogenchloride;

DOI:10.1021/jm0009181

Reference yield: 31.0%

dicyandiamide (127099-85-8,780722-26-1) + 4-chloro-aniline (106-47-8) + acetone (67-64-1) → cycloguanil hydrochloride (152-53-4)

Guidance literature:

With hydrogenchloride; for 24h; Heating;

DOI:10.1021/jm00368a006

upstream raw materials:

dicyandiamide

4-chloro-aniline

acetone

N-Cyanoguanidine

Refernces

• 1、 Ma, Xiang,Poon, Thong-Yuen,Wong, Peter Tsun Hon,Chui, Wai-Keung. "Synthesis and in vitro evaluation of 2,4-diamino-1,3,5-triazine derivatives as neuronal voltage-gated sodium channel blockers". supporting information; experimental part. p. 5644 - 5647. Retrieved 2010/04/26.
• 2、 Hansch,Hathaway,Guo,et al.. "Crystallography, quantitative structure-activity relationships, and molecular graphics in a comparative analysis of the inhibition of dihydrofolate reductase from chicken liver and Lactobacillus casei by 4,6-diamino-1,2-dihydro-2,2-dimethyl-1-(substituted-phenyl)-s-triazines". . p. 129 - 143. Retrieved 2007/10/02.