68000-92-0

Usage

Uses

Used in Pharmaceutical Industry:
Farnesyl cysteine is used as a key intermediate in the synthesis of various biologically active compounds, including drugs targeting specific signaling pathways. Its unique structure allows it to interact with cellular components, making it a valuable building block for the development of new therapeutic agents.
Used in Biochemical Research:
In the field of biochemical research, farnesyl cysteine serves as an important tool for studying the role of prenylation, a post-translational modification process that plays a crucial role in protein function and localization. Researchers use farnesyl cysteine to investigate the mechanisms of prenylation and its implications in various diseases, including cancer and neurodegenerative disorders.
Used in Cosmetic Industry:
Farnesyl cysteine has potential applications in the cosmetic industry due to its ability to modulate cellular processes and improve skin health. It can be used as an active ingredient in anti-aging products, where it may help to promote collagen production, reduce the appearance of fine lines and wrinkles, and maintain skin elasticity.
Used in Agricultural Industry:
In agriculture, farnesyl cysteine may be utilized as a component in the development of novel plant growth regulators or as a signaling molecule to enhance crop yield and resistance to various stressors. Its unique structure and properties make it a promising candidate for improving agricultural practices and crop management.

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

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

Downstream Products

• 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 
• 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 
• 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 
• 1227280-26-3 (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 
• 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 
• 1227280-80-9 2-(N-((R)-1-carboxy-2-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienylthio)ethyl)sulfamoyl)benzoic acid 
• 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 

Relevant academic research and scientific papers

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.

Functionalized indoleamines as potent, drug-like inhibitors of isoprenylcysteine carboxyl methyltransferase (Icmt)

The enzyme isoprenylcysteine carboxyl methyltransferase (Icmt) plays an important role in the post-translational modification of proteins involved in the regulation of cell growth and oncogenesis. The biological consequences of Icmt inhibition strongly implicate the enzyme as a potential therapeutic target for cancer and provide a compelling rationale for developing specific Icmt inhibitors as anti-cancer agents. We report here the systematic modification of the known Icmt inhibitor cysmethynil to give an analog 15 with greatly improved solubility and PAMPA permeability which was achieved with concurrent gains in Icmt inhibitory and cell-based antiproliferative activities. The modifications involved replacing the amide side chain of cysmethynil with a tertiary amine, and introducing an aminopyrimidine ring in place of m-tolyl. The presence of the weakly basic and polar aminopyrimidine ring contributed significantly to the potency and drug-like profile of the final compound.

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.

Synthesis and application in SPPS of a stable amino acid isostere of palmitoyl cysteine

(S)-2-Amino-4-(2-pentadecyl-1,3-dioxolan-2-yl)-butanoic acid, 11, Pdiob, a synthetic analogue C-isostere of palmitoylated cysteine, has been prepared starting from tetrabenzyl glutamic acid. The less hindered benzyl carboxylate ester was transformed into

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.

Solid-phase synthesis of lipidated peptides

Blockers, anchors, and reporters: A solid-phase method for the synthesis of lipidated peptides (see scheme) relies on the base-labile Fmoc group to block the N-terminus, an oxidation-labile hydrazide linker for anchoring to the solid support, and lipidate