122292-85-7

Basic information

• Product Name: (S)-(-)-trichostatin A
• Synonyms: (S)-(-)-trichostatin A
• CAS NO: 122292-85-7
• Molecular Weight: 302.373
• Mol File: 122292-85-7.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: (S)-(-)-trichostatin A(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-trichostatin A(122292-85-7)
• EPA Substance Registry System: (S)-(-)-trichostatin A(122292-85-7)

Safety Data

• Hazardous Substances Data: 122292-85-7(Hazardous Substances Data)

Usage

General Description

(S)-(-)-trichostatin A is a potent and specific inhibitor of histone deacetylases (HDACs), which are enzymes that remove acetyl groups from histone proteins, leading to transcriptional repression. (S)-(-)-trichostatin A has been extensively studied for its potential therapeutic applications in the treatment of cancer, neurological disorders, and other diseases. By inhibiting HDACs, (S)-(-)-trichostatin A can induce hyperacetylation of histone proteins, leading to changes in chromatin structure and gene expression. Its ability to modulate gene expression makes it a valuable tool for understanding epigenetic regulation and for developing novel therapies targeting epigenetic mechanisms. Additionally, (S)-(-)-trichostatin A has been used in research to study the role of histone acetylation in various biological processes, making it a valuable reagent for epigenetic studies.

Upstream product

• 1334686-47-3 C₂₃H₃₆N₂O₃Si 
• 114127-18-3 (+)-(R)-trichostatin acid 
• 921213-02-7 (2E,4E,6R)-7-[4-(dimethylamino)phenyl]-7-methoxy-4,6-dimethyl-2,4-heptadienoic acid 
• 1334686-43-9 4-[(2R)-1-methoxy-2-methylpent-3-yn-1-yl]-N,N-dimethylaniline 
• 1334686-42-8 4-[(2R)-1-methoxy-2-methylbut-3-yn-1-yl]-N,N-dimethylaniline 
• 1334686-41-7 (R)-1-[4-(dimethylamino)phenyl]-2-methylbut-3-yn-1-ol 
• 100-10-7 4-dimethylamino-benzaldehyde 
• 122222-84-8 methyl 4,6-(S)-dimethyl-7-(4'-N,N-dimethylaminophenyl)-7-(2-methoxypropyloxy)-2,4-heptadienoate 
• 122222-84-8 methyl 4,6-(R)-dimethyl-7-(4'-N,N-dimethylaminophenyl)-7-(2-methoxypropyloxy)-2,4-heptadienoate 
• 122222-74-6 3-t-butyldimethylsilyloxy-1-(4'-N,N-dimethylaminophenyl)-1-(2-methoxypropyloxy)-2-(R)-methylpropane 
• 122222-74-6 3-t-butyldimethylsilyloxy-1-(4'-N,N-dimethylaminophenyl)-1-(2-methoxypropyloxy)-2-(S)-methylpropane 
• 122222-79-1 ethyl 2,4-(S)-dimethyl-5-(4'-N,N-dimethylaminophenyl)-5-(2-methoxypropyloxy)-2-pentenoate 
• 122222-79-1 ethyl 2,4-(R)-dimethyl-5-(4'-N,N-dimethylaminophenyl)-5-(2-methoxypropyloxy)-2-pentenoate 
• 122222-85-9 4,6-(S)-dimethyl-7-(4'-N,N-dimethylaminophenyl)-7-hydroxy-2,4-heptadienoic acid 

Downstream Products

• 1298085-51-4 2,3-dihydrotrichostatin A 
• 68676-88-0 trichostatin C 

Relevant articles and documents

Evolution of concise and flexible synthetic strategies for trichostatic acid and the potent histone deacetylase inhibitor trichostatin A

(R)-(+)-Trichostatic acid and (R)-(+)-trichostatin A (TSA) are natural products that have attracted considerable attention in the field of epigenetic therapies. TSA in particular is a naturally occurring hydroxamic acid having potent activity as a histone deacetylase inhibitor (HDACi) and having significant potential for treatment of a myriad of genetically based diseases. Development of TSA and other trichostatic acid derivatives into useful small-molecule therapies has been hindered by the low natural abundance and high cost associated with these compounds. We report herein our collective efforts towards the development of concise and scalable routes for the synthesis of trichostatic acid and TSA in both racemic and enantioenriched forms. Three independent synthetic pathways were developed with varying degrees of efficiency and convergency. In the first synthesis, the key step was a vinylogous Horner-Wadsworth-Emmons condensation. A Marshall propargylation reaction was used as the key step in the second synthesis, and Pd-catalyzed α-alkenylation of a ketone zinc enolate by using various functionalized alkenyl or dienyl halides was developed for the third synthesis. The second pathway proved to be readily amenable to an enantioselective modification, and both the second and third pathways were straightforwardly adapted for the facile preparation of new analogues of trichostatic acid and TSA. Three synthetic strategies have been developed for trichostatic acid and trichostatin A. Each strategy has a different key bond-forming step; a vinylogous Horner-Wadsworth-Emmons condensation, a Marshall propargylation, and coupling of a ketone enolate with various alkenyl halides. Two of the syntheses were efficient and able to produce analogues. Two of the syntheses were enantioselective. Copyright

OCULAR HYPOTENSIVE AGENT COMPRISING COMPOUND CAPABLE OF INHIBITING HISTONE DEACETYLASE AS ACTIVE INGREDIENT

An object of the present invention is to find a novel pharmacological effect of a compound having an HDAC inhibitory effect. The compound having an HDAC inhibitory effect of the invention has an excellent effect of cell morphological change on trabecular meshwork cells and/or effect of intraocular pressure reduction, and is therefore useful as a preventive and/or therapeutic agent for a disease considered to be associated with aqueous humor circulation and/or intraocular pressure, particularly as a preventive and/or therapeutic agent for glaucoma or ocular hypertension.

Efficient, enantioselective organocatalytic synthesis of trichostatin A

An efficient, highly stereocontrolled total synthesis of trichostatin A (1) has been achieved in 9 steps with 17.4% overall yield and >99% optical purity from readily available achiral starting materials. The key features of this synthesis include the L-proline-promoted, highly enantioselective cross-aldol reaction as a crucial step for the construction of the C-6 chiral center and the minimization of racemization by final step oxidation of the OH group to a ketone at position 7.