CHS-828

Base Information

• Chemical Name: CHS-828
• CAS No.: 200484-11-3
• Molecular Formula: C19H22ClN5O
• Molecular Weight: 371.87
• Mol file: 200484-11-3.mol

Synonyms:Guanidine, N-(6-(4-chlorophenoxy)hexyl)-N-cyano-N-4-pyridinyl-;2-[6-(4-chlorophenoxy)hexyl]-3-cyano-1-pyridin-4-yl-guanidine;CHS 828;N-(6-(4-Chlorophenoxy)hexyl)-N-cyano-N-4-pyridinylguanidine;

Chemical Property of CHS-828

Chemical Property:

• Vapor Pressure: 3.44E-11mmHg at 25°C
• Refractive Index: 1.587
• Boiling Point: 526.9 °C at 760 mmHg
• PKA: 7.36±0.10(Predicted)
• Flash Point: 272.4 °C
• PSA: 82.33000
• Density: 1.18 g/cm³
• LogP: 4.80398
• Storage Temp.: ?20°C
• Solubility.: DMSO: soluble20mg/mL, clear

Purity/Quality:

99% ^*data from raw suppliers

GMX1778 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25-36/37/38
• Safety Statements: 26-45

MSDS Files:

SDS file from LookChem

Useful:

• Description: CHS-828 is a pyridyl cyanoguanidine anti-tumor agent that has been identified as a competitive inhibitor of Nampt as well as an inhibitor of NF-κB pathway activity. CHS-828 has potent cytotoxic effects in human breast (IC50 = 7.3 nM) and lung cancer (IC50 = 0.5 nM) cells both in vitro and in vivo. In nude mice bearing human tumor xenografts, CHS-828, at 20-50 mg/kg/day, inhibits the growth of MCF-7 breast cancer tumors and induces regression of NYH small cell lung cancer tumors.
• Uses: GMX1778 is an anticancer agent that inhibits cellular synthesis of NAD.

Technology Process of CHS-828

There total 5 articles about CHS-828 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: 89.0%

6-(4-chlorophenoxy)hexyl-1-amine (200484-41-9) + (Z)-N'-cyano-N-(pyridin-4-yl) methylsulfanylmethanimidamide (200483-99-4) → (E)-1-(6-(4-chlorophenoxy)hexyl)-2-cyano-3-(pyridin-4-yl)guanidine (200484-11-3)

Guidance literature:

With pyridine; dmap; triethylamine; at 55 ℃; for 5h;

DOI:10.1016/S0960-894X(97)10152-4

Reference yield: 57.0%

CYANAMID (420-04-2) + 1-[6-(4-Chloro-phenoxy)-hexyl]-3-pyridin-4-yl-thiourea → (E)-1-(6-(4-chlorophenoxy)hexyl)-2-cyano-3-(pyridin-4-yl)guanidine (200484-11-3)

Guidance literature:

With triethylamine; dicyclohexyl-carbodiimide; In acetonitrile; for 216h; Ambient temperature;

DOI:10.1016/S0960-894X(97)10152-4

Reference yield:

4-aminopyridine (504-24-5) → (E)-1-(6-(4-chlorophenoxy)hexyl)-2-cyano-3-(pyridin-4-yl)guanidine (200484-11-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / NaH / dimethylformamide; paraffin / 1.) 0 deg C, 6 h, 2.) room temperature, overnight

2: 89 percent / triethylamine, 4-dimethylaminopyridine, pyridine / 5 h / 55 °C

With pyridine; dmap; sodium hydride; triethylamine; In N,N-dimethyl-formamide; paraffin;

DOI:10.1016/S0960-894X(97)10152-4

upstream raw materials:

CYANAMID

6-(4-chlorophenoxy)hexyl-1-amine

(Z)-N'-cyano-N-(pyridin-4-yl) methylsulfanylmethanimidamide

4-aminopyridine

Downstream raw materials:

1-[N-(tert-butoxycarbonylmethyl)-carbamoyloxymethyl]-4-[N'-cyano-N-(6-(4-chlorophenoxy)-hexyl)-N-guanidino]-pyridinium iodide

1-[5-(N-tert-butoxycarbonylamino)-pentanoyloxymethyl]-4-[N'-cyano-N-(6-(4-chlorophenoxy)-hexyl)-N-guanidino]-pyridinium iodide

1-Pivaloyloxymethyl-4-[N'-cyano-N-(6-(4-chlorophenoxy)-hexyl)-N-guanidino]-pyridinium chloride

1-[3-(tert-butoxycarbonyl)-propionyloxymethyl]-4-[N'-cyano-N-(6-(4-chlorophenoxy)-hexyl)-N-guanidino]-pyridinium chloride

Refernces

• 1、 Chern, Jyh-Haur,Shia, Kak-Shan,Chang, Chung-Ming,Lee, Chung-Chi,Lee, Yen-Chun,Tai, Chia-Liang,Lin, Ying-Ting,Chang, Chih-Shiang,Tseng, Huan-Yi. "Synthesis and in vitro cytotoxicity of 5-substituted 2-cyanoimino-4- imidazodinone and 2-cyanoimino-4-pyrimidinone derivatives". . p. 1169 - 1172. Retrieved 2007/10/03.
• 2、 Schou, Charlotte,Ottosen, Erik R.,Petersen, Hans Jorgen,Bjoerkling, Fredrik,Latini, Scilla,Hjarnaa, Pernille V.,Bramm, Erik,Binderup, Lise. "Novel cyanoguanidines with potent oral antitumour activity". . p. 3095 - 3100. Retrieved 2007/10/03.