55284-67-8

Upstream product

• 27303-99-7 sodium menthoxide 
• 598-21-0 2-Bromoacetyl bromide 
• 2623-23-6 L-menthyl acetate 
• 2216-51-5 (-)-menthol 
• 79-08-3 bromoacetic acid 

Downstream Products

• 81983-62-2 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-(dimethylamino)acetate 
• 72774-16-4 (S)-3-hydroxy-3-phenyl-butyric acid-((1R)-menthyl ester) 
• 175671-51-9 (-)-5,11,17,23-tetra-tert-butyl-25-ethoxy-26,28-dihydroxy-27-<(1R,2S,5R)menthyloxycarbonylmethoxy>calix<4>arene 
• 125382-46-9 (1R,2S,5R)(-)-menthyl-4-chlorophenylsulfenylacetate 
• 26315-61-7 L-menthyl glyoxylate 
• 39169-54-5 (S)-3-hydroxy-3-(4'-methoxyphenyl)propanoic acid 
• 679818-54-3 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-(benzylamino)acetate 
• 1246513-51-8 (2-isopropyl-5-methylcyclohexyloxycarbonylmethyl)(3-methoxyphenyl)(naphthalen-1-yl)phenylphosphonium bromide 
• 75468-48-3 (L)-carbomenthyloxymethyl triphenylphosphonium bromide 

Relevant academic research and scientific papers

DERIVATIVES OF MENTHOL AND USES THEREOF

A compound that includes a menthol glycinate. The menthol glycinate includes a menthol connected to a glycine or glycine derivative, via an ester linkage. The groups on the N atom are referred to as R1 and R2, and R1 and R

A CONJUGATE OF A TUBULYSIN ANALOG WITH BRANCHED LINKERS

The present invention relates to the conjugation of a tubulysin analog compound to a cell-binding molecule with branched/side-chain linkers for having better delivery of the conjugate compound and targeted treatment of abnormal cells. It also relates to a branched-linkage method of conjugation of a tubulysin analog molecule to a cell-binding ligand, as well as methods of using the conjugate in targeted treatment of cancer, infection and autoimmune disease.

Site-Tunable Csp3 -H Bonds Functionalization by Visible-Light-Induced Radical Translocation of N-Alkoxyphthalimides

Site-tunable functionalization of C(sp3)-H bonds has been accomplished through radical translocation and cross-coupling. Upon irradiation with visible light, copper-based photocatalyst [Cu(Xantphos)(dmp)]BF4 enabled cross-coupling of N-alkoxyphthalimides with amino acid esters or amino acids to provide δ-C(sp3)-H alkylated alcohols (31 examples, up to 92% yield) with additive BNDHP or α-C(sp3)-H alkylated alcohols (18 examples, up to 86% yield) with additive DABCO in a highly regioselective fashion.

Cycloaddition of Fluorenone N-Aryl Nitrones with Methylenecyclopropanes and Sequential 1,3-Rearrangement: An Entry to Synthesis of Spirofluorenylpiperidin-4-ones

A facile synthesis of various spirofluorenylpiperidin-4-ones has been achieved in good yields from fluorenone N-aryl nitrones and methylenecyclopropanes. This method involved an initial cycloaddition to form a 5-spirocyclopropane-isoxazoline, which underwent a highly selective 1,3-rearrangement to give the desired product. The stereochemistry of the spirofluorenylpiperidin-4-one could be controlled by the cycloaddition and sequential rearrangement strategy. Furthermore, the spirofluorenylpiperidin-4-ones could be not only prepared in one-pot procedure but also converted to useful scaffolds by reduction or oxidation conditions.

Synthesis and Superpotent Anticancer Activity of Tubulysins Carrying Non-hydrolysable N-Substituents on Tubuvaline

Synthetic tubulysins 24 a–m, containing non-hydrolysable N-substituents on tubuvaline (Tuv), were obtained in high purity and good overall yields using a multistep synthesis. A key step was the formation of differently N-substituted Ile-Tuv fragments 10 b

Diastereoselective synthesis of a highly functionalized cyclohexene embedded with a quaternary stereogenic centre by self Diels-Alder dimerization of a [3]dendralene attached to a (-)-menthol auxiliary

A novel route to a chiral functionalized [3]dendralene attached to a (-)-menthol auxiliary has been developed, which involves a dimethylsulfonium methylide mediated olefination of a substituted ethenylidene phosphonoacetate (-)-menthyl ester, followed by

Solvent-Controlled Bifurcated Cascade Process for the Selective Preparation of Dihydrocarbazoles or Dihydropyridoindoles

A solvent-controlled cascade process has been identified for the dual purpose of the preparation of either dihydrocarbazoles or dihydropyridoindoles from identical N-aryl-α,β-unsaturated nitrones and electron-deficient allene starting materials. These reactions proceed smoothly under mild metal-free conditions affording a range of two types of skeletally distinct indole-based heterocycles in high yield and diastereoselectivity. These transformations demonstrate the use of a bifurcated cascade process that hinges on the ring-opening event of a benzazepine intermediate for the synthesis of skeletally diverse heterocyclic products and rapid access to biologically-significant, indole-based structures.

DENTOTROPIC CONJUGATES AND COMPOSITIONS AND METHODS OF USE THEREOF

Compositions and methods for targeting agents, particularly a flavoring, fragrant, or cooling agent such as menthol, to tooth are provided. The success of delivering biologically active agents to the oral cavity has been largely limited by the fact that m

Synthesis and structure-activity relationship studies of novel tubulysin U analogues-effect on cytotoxicity of structural variations in the tubuvaline fragment

Tubulysins are cytotoxic natural products with promising anti-cancer properties, originally isolated from myxobacterial cultures. Structurally, tubulysins are tetrapeptides, incorporating three unusual (Mep, Tuv and Tup) and one proteinogenic amino acid (Ile). Here we describe the synthesis and structure-activity relationship studies of novel tubulysin U and V analogues, with variations in the central Tuv fragment, which is known to be of paramount importance for tubulysins' potency and hence cytotoxicity, but has seldom been modified in previous studies. Specifically, we replaced the natural iso-propyl and acetoxy functionalities with other structurally related groups. In general, the new analogues showed much lower potency relative to native tubulysin U. However, one of the synthetic analogues (1f) having a MOM function replacing the acetyl group exhibited a 22 nM IC50 on the HT-29 cell line which is comparable to the IC50 displayed by tubulysin U (3.8 nM). Furthermore, the synthetic methodology reported herein was found to be flexible enough to deliver different core-modified tubulysin analogues and hence may be regarded as a scalable and convenient strategy for the chemical generation of novel tubulysin analogues.

Synthesis and cytotoxicity evaluation of diastereoisomers and N-terminal analogues of tubulysin-U

Tubulysins are potent anti-mitotic natural compounds and a scalable and efficient synthetic route for generation of its analogues has been developed and extended to the synthesis of diastereoisomers and N-terminal analogues of tubulysin-U. Structure-activ