4282-78-4

Usage

Uses

Used in Pharmaceutical Synthesis:
10-(2-Propyn-1-yl)-10H-phenothiazine is used as an intermediate in the synthesis of Promethazine and some of its metabolites. Promethazine is a phenothiazine-derivative antihistamine used to treat various conditions, such as allergies, motion sickness, and nausea. 10-(2-Propyn-1-yl)-10H-phenothiazine's unique structure allows for the development of new pharmaceuticals with potential therapeutic benefits.
Used in Chemical Research:
As a phenothiazine derivative, 10-(2-Propyn-1-yl)-10H-phenothiazine can be utilized in chemical research to explore the properties and potential applications of phenothiazine-based compounds. This may include studying their interactions with other molecules, understanding their reactivity, and developing new synthetic methods for their preparation.
Used in Material Science:
10-(2-Propyn-1-yl)-10H-phenothiazine's white solid form and unique chemical structure may also make it a candidate for use in material science, where it could be investigated for potential applications in the development of new materials with specific properties, such as optical, electronic, or mechanical characteristics.

Upstream product

• 92-84-2 10H-phenothiazine 
• 106-96-7 propargyl bromide 

Downstream Products

• 15375-61-8 6-phenothiazin-10-yl-1,1-diphenyl-hexa-2,4-diyn-1-ol 
• 15375-56-1 1-(10H-phenothiazin-10-yl)propan-2-one 
• 1374749-77-5 C₂₆H₁₉NO₂S 
• 1374749-78-6 C₃₅H₂₆BrNO₄S 
• 1374749-82-2 C₅₈H₄₁N₃O₆S 
• 1374749-76-4 C₂₄H₁₈BrNO₂S 

Relevant academic research and scientific papers

One-Pot Regioselective Synthesis of Some Novel Isoxazole-Phenothiazine Hybrids and Their Antibacterial Activity

Abstract: Some novel isoxazole-phenothiazine hybrids have been synthesized regioselectively in high yields via Cu(I) catalyzed one-pot reaction of 10-(prop-2-yn-1-yl)phenothiazine with aromatic aldehydes in aqueous butanol medium. Structures of the newly

Multidrug resistance reverting activity and antitumor profile of new phenothiazine derivatives

A series of easily affordable phenothiazine derivatives bearing a rigid but-2-ynyl amino side chain were synthesized and tested to evaluate the MDR reverting activity and full antitumor profile. Some compounds endowed with remarkable MDR reverting effect were identified, and the most active one (6c) was shown to increase doxorubicin retention in multidrug resistant cells, suggesting a direct interaction with P-glycoprotein. Furthermore, a broad range of cellular activities were observed for different compounds. In particular, the ability of some derivatives to induce antiproliferative effects on resistant cell lines and to interfere with the G1 phase of the cell cycle, a phase usually not affected by classical antitumor agents, was noted. Moreover, the most cytotoxic compounds of the series were able to induce apoptosis in resistant cell lines, via an atypical pathway of caspase cascade activation, and a synergistic effect in combination with doxorubicin was also found.

Synthesis of Molecular Dyads and Triads Based Upon N-Annulated Perylene Diimide Monomers and Dimers

The synthesis of N-annulated perylene diimides (NPDIs) with grafted electron donating phenothiazine (PTZ) groups is presented. The synthetic strategy takes advantage of the N-annulation at the PDI bay position, which allows for the facile installation of the pendant donors. Three new molecular materials are reported, a dyad consisting of an NPDI monomer tethered to a PZT unit (4), a dyad consisting of an NPDI dimer with one PZT unit tethered (9), and a triad consisting of an NPDI dimer with two PTZ units tethered (10). The PTZ and NPDI were “clicked” together using copper catalyzed alkyne–azide cycloaddition chemistry. Analysis of optical absorption/emission spectra and electrochemical data reveal that the electronic structure of each individual aromatic system remains distinct, but through-space interactions occur, as is evident by fluorescence quenching in both solution and the solid state.

Molecular diversity of trimethoxyphenyl-1,2,3-triazole hybrids as novel colchicine site tubulin polymerization inhibitors

Structurally diverse trimethoxyphenyl-1,2,3-triazole hybrids were designed, synthesized and evaluated for their antiproliferative activity against three cancer cell lines (PC3, MGC803 and HepG2). Among them, trimethoxyphenyl-1,2,3-triazole containing the

Molecular hybridization approach for phenothiazine incorporated 1,2,3-triazole hybrids as promising antimicrobial agents: Design, synthesis, molecular docking and in silico ADME studies

The objective of the current study is to synthesize a library consisting of four sets of phenothiazine incorporated 1,2,3-triazole compounds using molecular hybridization approach. In total, 36 new hybrid molecules were synthesized and screened for in vitro growth inhibition activity against Mycobacterium tuberculosis H37Rv strain (ATCC-27294). Among the tested compounds, nineteen compounds exhibited significant activity with MIC value 1.6 μg/mL, which is twofold higher than the MIC value of standard first-line TB drug Pyrazinamide. In addition, all these compounds are proved to be non-toxic (with selective index > 40) against VERO cell lines. However, these compounds did not inhibit significantly the growth of Staphylococcus aureus, Escherichia coli, and Pseudomonas aeruginosa strains: the activity profile is similar to that observed for standard anti-TB drugs (isoniazid and pyrazinamide), indicating the specificity of these compounds towards the Mycobacterium tuberculosis strain. Also, we report the molecular docking studies against two target enzymes (Inh A and CYP121) to further validate the antitubercular potency of these molecules. Furthermore, prediction of in silico-ADME and pharmacokinetic parameters indicated that these compounds have good oral bioavailability. The results suggest that these phenothiazine incorporated 1,2,3-triazole compounds are a promising class of molecular entities for the development of new antitubercular leads.

Antitumor evaluation of novel phenothiazine derivatives that inhibit migration and tubulin polymerization against gastric cancer MGC-803 cells

Two novel series of 1,2,3-triazole?phenothiazine hybrids and dithiocarbamate?phenothiazine hybrids were designed and synthesized by molecular hybridization strategy. Their antiproliferative activity against three gastric cancer cell lines (MKN28, MGC-803

Development of a Focused Library of Triazole-Linked Privileged-Structure-Based Conjugates Leading to the Discovery of Novel Phenotypic Hits against Protozoan Parasitic Infections

Protozoan infections caused by Plasmodium, Leishmania, and Trypanosoma spp. contribute significantly to the burden of infectious diseases worldwide, causing severe morbidity and mortality. The inadequacy of available treatments calls for cost- and time-ef

Antiproliferative phenothiazine hybrids as novel apoptosis inducers against MCF-7 breast cancer

We designed a series of novel phenothiazine-1,2,3-triazole hybrids by the molecular hybridization strategy and evaluated their antiproliferative activity against three cancer cell lines (MDA-MB-231, MDA-MB-468 and MCF-7). For the structure-activity relationships, the importance of 1,2,3-triazole and substituents on phenyl ring was explored. Among these phenothiazine-1,2,3-triazole hybrids, compound 9f showed the most potent inhibitory effect against MCF-7 cells, with an IC50 value of 0.8 μM. Importantly, compound 9f could induce apoptosis against MCF-7 cells by regulating apoptosis-related proteins (Bcl-2, Bax, Bad, Parp, and DR5). These potent phenothiazine-1,2,3-triazole hybrids as novel apoptosis inducers might be used as antitumor agents in the future.

Enhanced performance of dye-sensitized solar cell using triazole based phenothiazine dendrimers as additives

Phenothiazine dendritic architectures with 1,2,3-triazole as a bridging unit are synthesized through a convergent approach using click chemistry and when used as additives in dye-sensitized solar cells (DSSCs) show increased efficiency in solar energy harvesting systems. The presence of a greater number of phenothiazine and triazole units increased the molar absorption coefficient and fluorescence quantum yields. In DSSCs, the redox couple doped with first generation triazole based phenothiazine dendrimers showed a higher V oc voltage through the suppression of back electron transfer and exhibited a better power conversion efficiency (η) of 8.6% under 70 mW cm-2 irradiation than the zeroth generation dendrimers. The Royal Society of Chemistry.

HYDROBORATION D'AMINES INSATUREES. V. NOUVELLE VOIE D'ACCES AUX AMIOALKYLIDENECYCLOALKANES

Hydroboration of various 1-bromopropargylamines by borinane and 3,6-dimethylborepane has led to α-bromovinylboranes.Treatment of these compounds with iodine in basic media, only gives aminoalkylidenecycloalkanes with excellent yields.