68000-92-0

Basic information

• Product Name: FARNESYL CYSTEINE
• Synonyms: FARNESYL CYSTEINE;S-farnesylcysteine;S-[(2E,6E)-farnesyl]-L-cysteine
• CAS NO: 68000-92-0
• Molecular Formula: C₁₈H₃₁NO₂S
• Molecular Weight: 325.51
• Mol File: 68000-92-0.mol
• Article Data: 7

Chemical Properties

• Melting Point: 148-150 °C
• Boiling Point: 473.3°Cat760mmHg
• Flash Point: 240°C
• Appearance: /
• Density: 1.021g/cm³
• Vapor Pressure: 2.9E-10mmHg at 25°C
• Refractive Index: 1.528
• PKA: 2.08±0.10(Predicted)
• CAS DataBase Reference: FARNESYL CYSTEINE(CAS DataBase Reference)
• NIST Chemistry Reference: FARNESYL CYSTEINE(68000-92-0)
• EPA Substance Registry System: FARNESYL CYSTEINE(68000-92-0)

Safety Data

• Hazardous Substances Data: 68000-92-0(Hazardous Substances Data)

Usage

Definition

ChEBI: An S-farnesyl-L-cysteine where the C2C double bonds at the 2- and 6-positions both have (E)-configuration.

InChI:InChI=1/C18H31NO2S/c1-14(2)7-5-8-15(3)9-6-10-16(4)11-12-22-13-17(19)18(20)21/h7,9,11,17H,5-6,8,10,12-13,19H2,1-4H3,(H,20,21)/b15-9+,16-11+/t17-/m0/s1

Upstream product

• 130062-64-5 methyl S-farnesylcysteine 
• 52-90-4 L-Cysteine 
• 24163-93-7 farnesyl bromide 
• 6784-45-8 (2E,6E)-farnesyl chloride 

Downstream Products

• 1227280-32-1 (6S,9R,13E,17E)-6-cyclohexyl-2,2,14,18,22-pentamethyl-4,7-dioxo-3-oxa-11-thia-5,8-diazatricosa-13,17,21-triene-9-carboxylic acid 
• 1227280-80-9 2-(N-((R)-1-carboxy-2-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienylthio)ethyl)sulfamoyl)benzoic acid 
• 1227281-35-7 (1R,2S)-2-((R)-1-carboxy-2-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienylthio)ethylcarbamoyl)cyclohexanecarboxylic acid 
• 1227281-34-6 (1S,2R)-2-((R)-1-carboxy-2-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienylthio)ethylcarbamoyl)cyclohexanecarboxylic acid 
• 1227280-26-3 (6S,9R,13E,17E)-2,2,14,18,22-pentamethyl-4,7-dioxo-6-phenyl-3-oxa-11-thia-5,8-diazatricosa-13,17,21-triene-9-carboxylic acid 
• 1227280-30-9 (6R,9R,13E,17E)-6-benzhydryl-2,2,14,18,22-pentamethyl-4,7-dioxo-3-oxa-11-thia-5,8-diazatricosa-13,17,21-triene-9-carboxylic acid 
• 1227280-38-7 (R)-2-((S)-5-benzyloxy-2-(tert-butoxycarbonylamino)-5-oxopentanamido)-3-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienylthio)propanoic acid 
• 191022-22-7 2-(tert-butoxycarbonylamino)-3-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienylthio)propanoic acid 
• 135304-07-3 N-acetyl-S-trans,trans-farnesyl-L-cysteine 

Relevant articles and documents

Synthetic optimization and mapk pathway activation anticancer mechanism of polyisoprenylated cysteinyl amide inhibitors

Abnormalities of the MAPK pathway play vital roles in cancer initiation and progression. RAS GTPases that are key upstream mediators of the pathway are mutated in 30% of human cancers. Polyisoprenylated cysteinyl amide inhibitors (PCAIs) were designed as potential targeted therapies against the RAS-driven cancers. The current study reports on the optimization of the PCAIs and the determination of their mechanisms of action in KRAS-mutant cancer cells. They display ClogP values ranging from 3.01 to 6.35, suppressing the viabilities of KRAS-mutant MDA-MB-231, A549, MIA PaCa-2, and NCI-H1299 cells in 2D and 3D cultures with EC50 values of 2.2 to 6.8, 2.2 to 7.6, 2.3 to 6.5 and 5.0 to 14 μM, respectively. When A549 cells were treated with the PCAIs, NSL-YHJ-2-27, for 48 h, no significant difference was observed in the levels of total or phosphorylated B-and C-Raf proteins. However, at 5 μM, it stimulated the phosphorylation of MEK1/2, ERK1/2, and p90RSK by 84%, 59%, and 160%, respectively, relative to controls. A non-farnesylated analog, NSL-YHJ-2-62, did not elicit similar effects. These data reveal that effects on the RAS-MAPK signaling axis most likely contribute to the anticancer effects of the PCAIs, possibly through the proapoptotic isoforms of p90RSK. The PCAIs may thus have the potential to serve the unmet therapeutic needs of patients with aberrant hyperactive G-protein signaling.

Efficient S-alkylation of cysteine in the presence of 1,1,3,3- tetramethylguanidine

The synthesis of S-alkylated cysteine derivatives was carried out successfully in the presence of 1,1,3,3-tetramethylguanidine. Alkylation proceeded in high yields on unprotected amino acids and peptides containing a sulfhydryl group.

INHIBITORS OF ISOPRENYLCYSTEINE CARBOXYL METHYLTRANSFERASE

The present invention relates, in general, to isoprenylcysteine carboxyl methyltransferase (Icmt) and, in particular, to inhibitors of Icmt and to methods of disease treatment using same.