CarbaMiMidothioic acid, 3-cyanopropyl ester, hydrochloride (1:1)

CarbaMiMidothioic acid, 3-cyanopropyl ester, hydrochloride (1:1) Property

Melting point:

125-127 °C

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

solubility 

DMSO:38.0(Max Conc. mg/mL);211.5(Max Conc. mM)
Water:36.0(Max Conc. mg/mL);200.37(Max Conc. mM)
Ethanol:21.0(Max Conc. mg/mL);116.88(Max Conc. mM)
PBS (pH 7.2):10.0(Max Conc. mg/mL);55.66(Max Conc. mM)

form 

A crystalline solid

color 

White to off-white

Water Solubility 

H2O: 2mg/mL, clear

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

CarbaMiMidothioic acid, 3-cyanopropyl ester, hydrochloride (1:1) Chemical Properties,Usage,Production

Uses

4-Isothioureidobutyronitrile-13C2, 15N3 Hydrochloride acts as a reagent in the synthesis of nitrile derivatives and their pharmaceutical uses and compositions.

Biological Activity

Kevetrin is an activator/stabilizer of wild type p53 tumor suppressor protein in human lung carcinoma and ovarian cancer cells th at induces cell cycle arrest and apoptosis. Additionally Kevetrin down-regulates oncogenic mutant p53 in OVCAR-3 ovarian cancer cells. Kevetrin inhibits tumor growth in xenograft model of ovarian cancer.

Synthesis

General procedure for the synthesis of 3-cyanopropylisothiourea hydrochloride from 4-chlorobutanenitrile and thiourea: γ-chlorobutanenitrile (50 g, 48±3 mmol) and thiourea (4.04 g, 53.1 mmol) were dissolved in 40 mL of water. The reaction mixture was heated to reflux for 3 to 4 hours. After completion of the reaction, the water was removed by evaporation, 20 mL of ethanol was added and evaporated again, and this operation was repeated three times. Subsequently, 10 mL of methanol and 30 mL of acetone were added to the residue and the mixture was stirred for 1 hour. The crystalline product was collected by filtration and dried under high vacuum overnight. A final 5.44 g (30.3 mmol, yield 62 ± 7%) of white crystalline product was obtained with a melting point of 134-135 °C and a purity greater than 97%. The product was confirmed by 1H NMR (300 MHz, d6-DMSO): δ 1.89 (m, 2H), 2.63 (t, 2H, J = 7.2 Hz), 3.23 (t, 2H, J = 7.2 Hz), 3.38 (s, 3H). 13C NMR (75 MHz, d6-DMSO) δ 15.3, 25.0, 28.8, 119.8 , 169.7. molecular formula C5H10ClN3S, exact mass 179.03. mass spectral analysis showed m/z 179.03 (100.0%), 181.03 (32.1%), 180.03 (7.4%), 181.02 (4.5%), 182.03 (2.0%), 183.02 (1.5%). Elemental analysis calculated values (%): C 33.42, H 5.61, Cl 19.73, N 23.39, S 17.85; measured values: C 33.44, H 5.48, N 23.40, S 18.31.

in vivo

References

[1] Patent: WO2010/135170, 2010, A2. Location in patent: Page/Page column 20-21