150350-28-0

Basic information

• Product Name: 3-(tritylthio)propanal
• CAS NO: 150350-28-0
• Molecular Formula: C₂₂H₂₀OS
• Molecular Weight: 332.46
• Mol File: 150350-28-0.mol

Chemical Properties

• CAS DataBase Reference: 3-(tritylthio)propanal(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(tritylthio)propanal(150350-28-0)
• EPA Substance Registry System: 3-(tritylthio)propanal(150350-28-0)

Safety Data

• Hazardous Substances Data: 150350-28-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Chemistry:
3-(tritylthio)propanal is employed as a reagent in organic chemistry for its ability to selectively protect functional groups during chemical reactions. This selective protection is vital for the synthesis of complex organic molecules, where the integrity of certain groups must be preserved to achieve the desired final product.
Used in Pharmaceutical Development:
In the pharmaceutical industry, 3-(tritylthio)propanal is used as a key intermediate in the development of new drugs. Its protective properties allow chemists to carry out multi-step syntheses with greater precision, facilitating the creation of novel medicinal compounds with potential therapeutic benefits.
Used in Material Science:
3-(tritylthio)propanal also finds application in material science, where it contributes to the synthesis of advanced materials with specific properties. 3-(tritylthio)propanal's role in protecting functional groups is essential in the development of materials with tailored characteristics for various high-tech applications.
Used in Biological Research:
Furthermore, 3-(tritylthio)propanal has been investigated for its potential pharmacological properties, including its ability to modulate biological processes. This research opens up possibilities for the compound to be utilized in the study and treatment of various diseases and conditions, expanding its use beyond traditional chemical applications.

Upstream product

• 3695-77-0 triphenylmethanethiol 
• 500309-29-5 methyl 3-(tritylthio)-1-propanoate 
• 27144-18-9 3-(tritylthio) propanoic acid 
• 76-83-5 trityl chloride 
• 76-84-6 triphenylmethyl alcohol 
• 100360-56-3 3-(tritylthio)propan-1-ol 
• 107-02-8 acrolein 

Downstream Products

• 1309766-86-6 ethyl (E)-5-(triphenylmethylthio)-2-pentenoate 
• 180973-22-2 (2E)-5-[(triphenylmethyl)thio]-2-pentenal 
• 1043577-34-9 (S,E)-2-(trimethylsilyl)ethyl 3-(((S)-2-((R)-2'-(((tert-butoxycarbonyl)amino)methyl)-4-methyl-4,5-dihydro[2,4'-bithiazole]-4-carboxamido)-3-methylbutanoyl)oxy)-7-(tritylthio)hept-4-enoate 

Relevant articles and documents

Synthesis and preliminary biological evaluation of two fluoroolefin analogs of largazole inspired by the structural similarity of the side chain unit in psammaplin A

Largazole, isolated from a marine Cyanobacterium of the genus Symploca, is a potent and selective Class I HDAC (histone deacetylation enzymes) inhibitor. This natural 16-membered macrocyclic depsipeptide features an interesting side chain unit, namely 3-hydroxy-7-mercaptohept-4-enoic acid, which occurs in many other natural sulfur-containing HDAC inhibitors. Notably, one similar fragment, where the amide moiety replaces the trans alkene moiety, appears in Psammaplin A, another marine natural product with potent HDAC inhibitory activities. Inspired by such a structural similarity, we hypothesized the fluoroolefin moiety would mimic both the alkene moiety in Largazole and the amide moiety in Psammaplin A, and thus designed and synthesized two novel fluoro olefin analogs of Largazole. The preliminary biological assays showed that the fluoro analogs possessed comparable Class I HDAC inhibitory effects, indicating that this kind of modification on the side chain of Largazole was tolerable.

Synthesis and HDAC inhibitory activity of isosteric thiazoline-oxazole largazole analogs

The synthesis of an isosteric analog of the natural product and HDAC inhibitor largazole is described. The sulfur atom in the thizaole ring of the natural product has been replaced with an oxygen atom, constituting an oxazole ring. The biochemical activity and cytotoxicity of this species is described.

Addition of Sialic Acid to Insulin Confers Superior Physical Properties and Bioequivalence

Native insulin is susceptible to biophysical aggregation and fibril formation, promoted by manual agitation and elevated temperatures. The safety of the drug and its application to alternative forms of administration could be enhanced through the identification of chemical modifications that strengthen its physical stability without compromising its biological properties. Complex polysialic acids (PSAs) exist naturally and provide a means to enhance the physical properties of peptide therapeutics. A set of insulin analogues site-specifically derivatized with sialic acid were prepared in an overall yield of 50-60%. Addition of a single or multiple sialic acids conferred remarkable enhancement to the biophysical stability of human insulin while maintaining its potency. The time to the onset of fibrillation was extended by more than 10-fold relative to that of the native hormone. These results demonstrate that simplified sialic acid conjugates represent a viable alternative to complex natural PSAs in increasing the stability of therapeutic peptides.

C18-site fluoro Largazole analog, preparation method and application in preparation of antitumor agents

The invention belongs to the pharmaceutical field, and relates to a preparation method and pharmaceutical application of a fluorinated analogue of natural marine product cyclodepsipeptide (namely natural marine product Largazole) shown in the formula (I). The inhibitory activity test of HDACs in vitro shows that the compound of the invention has a strong and selective inhibitory effect on HDACs. Furthermore, drugs or compositions containing the compound of the present invention can be used to prepare anti-tumor therapeutic agents. The formula is shown in the description.

A fluorine scan on the Zn2+-binding thiolate side chain of HDAC inhibitor largazole: Synthesis, biological evaluation, and molecular modeling

Based on the unique role of a common unit in a family of sulfur-containing natural histone deacetylases (HDACs) inhibitors, we have chosen largazole as an example of these inhibitors and adopted a “fluorine scan” strategy towards modification of this common unit. Thus a set of fluoro largazole analogues has been designed, synthesized and evaluated in enzymatic as well as cellular assays. The preliminary results indicate that introduction of fluorine at the various position of the unit has an important impact on the activity and selectivity of HDACs. Unlike other modifications which often led to significant reduction or complete loss of activity as reported in the literature, most of these fluoro thiols have displayed comparable or enhanced activity and selectivity in enzymatic assays. Two of the sulfhydryl esters have also exhibited excellent inhibitory activity in cellular assays with a few selected cell lines. The C19-fluorinated analogue has been further studied by immunoblot analysis, confirming that it is a potent selective class I HDAC inhibitor and supporting that the potent cellular antiproliferative activity is due to HDAC inhibition. The molecular docking study reveals that introducing fluorine at the C19 position does not change the original interactions, but might have made a subtle change in binding conformation, resulting in an obvious improvement in activity.

HSP90-TARGETING CONJUGATES AND FORMULATIONS THEREOF

Conjugates of an active agent attached to a targeting moiety, such as an HSP90 binding moiety, via a linker, and particles comprising such conjugates have been designed. Such conjugates and particles can provide improved temporospatial delivery of the active agent, improved biodistribution and penetration in tumor, and/or decreased toxicity. Methods of making the conjugates, the particles, and the formulations thereof are provided. Methods of administering the formulations to a subject in need thereof are provided, for example, to treat or prevent cancer.

Radical-Mediated Thiol-Ene Strategy: Photoactivation of Thiol-Containing Drugs in Cancer Cells

Photoactivated drugs provide an opportunity to improve efficacy alongside reducing side-effects in the treatment of severe diseases such as cancer. Described herein is a photoactivation decaging method of isobutylene-caged thiols through a UV-initiated thiol-ene reaction. The method was demonstrated with an isobutylene-caged cysteine, cyclic disulfide-peptide, and thiol-containing drug, all of which were rapidly and efficiently released under mild UV irradiation in the presence of thiol sources and a photoinitiator. Importantly, it is shown that the activity of histone deacetylase inhibitor largazole can be switched off when stapled, but selectively switched on within cancer cells when irradiated with non-phototoxic light.

Synthesis of Naphthyridine Carbamate Dimer (NCD) Derivatives Modified with Alkanethiol and Binding Properties of G-G Mismatch DNA

A series of new DNA binding molecules NCD-Cn-SH (n = 3, 4, 5, and 6) is reported, which possesses the NCD (naphthyridine carbamate dimer) domain selectively binding to the G-G mismatch in the 5′-CGG-3′/5′-CGG-3′ sequence and a thiol moiety, which undergoes spontaneous dimerization to (NCD-Cn-S)2 upon oxidation under aerobic conditions. The S-S dimer (NCD-Cn-S)2 produced the 1:1 binding complex with improved thermal stability. The dimer binding to the CGG/CGG DNA showed higher positive cooperativity than the binding of monomer and previously synthesized NCTn derivative. The dimerization of NCD-Cn-SH was selectively accelerated on the CGG repeat DNA but not on the CAG repeat DNA.

AN IMPROVED PROCESS FOR THE PREPARATION OF (1S, 4S, 7Z, 10S, 16E, 21R)- 7-ETHYLIDENE-4,21-BIS(1-METHYLETHYL)-2-OXA-12,13-DITHIA-5, 8, 20, 23- TETRAAZABICYCLO[8.7.6]TRICOS-16-ENE-3, 6, 9, 19, 22-PENTONE

The present invention is relates to an improved process for the preparation (1S,4S,7Z,10S,16E,21R)-7-ethylidene-4,21-bis(1-methylethyl)-2-oxa-12,13-dithia-5,8,20,23-tetraazabi-cyclo[8.7.6]tricos-16-ene-3,6,9,19,22-pentone of formula I.

Sulfur-Switch Ugi Reaction for Macrocyclic Disulfide-Bridged Peptidomimetics

A general strategy is introduced for the efficient synthetic access of disulfide linked artificial macrocycles via a Ugi four-component reaction (U4CR) followed by oxidative cyclization. The double-mercapto input is proposed for use in the Ugi reaction, thereby yielding all six topologically possible combinations. The protocol is convergent and short and enables the production of novel disulfide peptidomimetics in a highly general fashion.