324519-54-2

Usage

Uses

Used in Organic Synthesis:
5-[Isocyano-(toluene-4-sulfonyl)-methyl]-1,2,3-trimethoxy-benzene is used as a reactive intermediate in organic synthesis for the preparation of various complex organic molecules. Its unique functional groups allow for versatile chemical reactions, facilitating the synthesis of a wide range of compounds with potential applications in various industries.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 5-[Isocyano-(toluene-4-sulfonyl)-methyl]-1,2,3-trimethoxy-benzene is used as a key building block in the development of new drugs. Its unique structure and reactivity make it an attractive candidate for the synthesis of novel pharmaceutical agents with potential therapeutic applications.
Used in Chemical Research:
5-[Isocyano-(toluene-4-sulfonyl)-methyl]-1,2,3-trimethoxy-benzene is also used as a research tool in chemical laboratories to study the properties and reactivity of complex organic compounds. Its unique structure provides insights into the behavior of various functional groups and their interactions with other molecules, contributing to the advancement of chemical knowledge and the development of new synthetic methods.

InChI:InChI=1/C18H19NO5S/c1-12-6-8-14(9-7-12)25(20,21)18(19-2)13-10-15(22-3)17(24-5)16(11-13)23-4/h6-11,18H,1,3-5H3

Upstream product

• 824-79-3 sodium 4-methylbenzenesulfinate 
• 951-82-6 3,4,5-trimethoxyphenyl acetic acid 
• 104-15-4 toluene-4-sulfonic acid 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 536-57-2 p-toluene sulfinic acid 
• 324519-53-1 N-{[(4-methylphenyl)sulfonyl](3,4,5-trimethoxyphenyl)methyl}formamide 

Downstream Products

• 1462267-50-0 1-methyl-4-(3,4,5-trimethoxyphenyl)-5-(2-methylthiophenyl)imidazole 
• 1462267-49-7 4-(3,4,5-trimethoxyphenyl)-5-(2-methylthiophenyl)oxazole 
• 1627130-74-8 4-(3,4,5-trimethoxyphenyl)-5-(4-methoxyphenyl)-1-ethylimidazole 
• 1352428-94-4 C₂₀H₂₂N₂O₄ 
• 1403581-29-2 4-(3,4,5-trimethoxyphenyl)-5-(4-methoxy-1H-benzo[d]imidazole-7-yl) oxazole 

Relevant academic research and scientific papers

The base-free van Leusen reaction of cyclic imines on water: Synthesis of N-fused imidazo 6,11-dihydro β-carboline derivatives

Construction of imidazoles has been demonstrated on water under base-free conditions. The reaction of dihydro β-carboline imines and p-toluenesulfonylmethyl isocyanides furnished the corresponding substituted N-fused imidazo 6,11-dihydro β-carboline derivatives in very good yields under ambient conditions. The use of deuterium oxide (D2O) as a solvent enabled the incorporation of deuterium isotopes in the imidazole ring.

Design, synthesis, and biological evaluation of novel combretastatin A-4 thio derivatives as microtubule targeting agents

A series of novel combretastatin A-4 (CA-4) thio derivatives containing different molecular cores, namely α-phenylcinnamic acids (core 1), (Z)-stilbenes (core 2), 4,5-disubstituted oxazoles (core 3), and 4,5-disubstituted N-methylimidazoles (core 4), as cis-restricted analogues were designed and synthesized. They were selected with the use of a parallel virtual screening protocol including the generation of a virtual combinatorial library based on an elaborated synthesis protocol of CA-4 analogues. The selected compounds were evaluated for antiproliferative activity against a panel of six human cancer cell lines (A431, HeLa, MCF7, MDA-MB-231, A549 and SKOV) and two human non-cancer cell lines (HaCaT and CCD39Lu). Moreover, the effect of the test compounds on the inhibition of tubulin polymerization in vitro was estimated. In the series studied here, oxazole-bridged analogues exhibited the most potent antiproliferative activity. Compounds 23a, 23e, and 23i efficiently inhibited tubulin polymerization with IC50 values of 0.86, 1.05, and 0.85 μM, respectively. Thio derivative 23i, when compared to its oxygen analogue 23j, showed a 5-fold higher inhibitory impact on tubulin polymerization. Compounds 23e and 23i, which showed both best cytotoxic and antitubulin activity, were further studied in terms of their effect on cell cycle distribution and proapoptotic activity. Compound 23e induced a statistically significant block of the cell cycle at the G2/M phase in A431, HaCaT, HeLa, MCF-7, MDA-MB-231, and SKOV-3 cells to an extent comparable to that observed in CA-4. In HeLa and SKOV-3 cells incubated with 23i, a concentration-dependent block of the G2/M phase was observed. The proapoptotic effect of 23e and 23i in A431, HaCaT, MCF-7, MDA-MB-231, and SKOV-3 was demonstrated with ELISA assay and double staining with Annexin V-FITC/PI. The results indicated that compound 23e and 23i may serve as novel lead compounds in research on more effective anticancer agents.

THE NEW DERIVATIVES OF (Z)-1,2-DIPHENYLETHENE

The present invention relates to the new chemical compounds containing (Z)-1,2-diphenylethene moiety in the structures, particularly the new derivatives of cis-stilbene, the new derivatives of 4,5-diphenyl-1,3-oxazole, the new derivatives of 1-methyl-4,5-diphenyl-1H-imidazole and pharmaceutically acceptable salts thereof. The invention relates also to the application of aforementioned compounds as a microtubule-interfering agents (MIAs). The new derivatives, because of their potential antimitotic and antiangio-genic activity, can be used as ingredients in the preparations used in the treatment of cancer.

THE NEW DERIVATIVES OF (Z)-1,2-DIPHENYLETHENE

The present invention relates to the new chemical compounds containing (Z)-1,2- diphenylethene moiety in the structures, particularly the new derivatives of cis-stilbene, the new derivatives of 4,5-diphenyl-1,3-oxazole, the new derivatives of 1-methyl-4,5-diphenyl-1H-imidazole and pharmaceutically acceptable salts thereof. The invention relates also to the application of aforementioned compounds as a microtubule-interfering agents (MIAs). The new derivatives, because of their potential antimitotic and antiangio-genic activity, can be used as ingredients in the preparations used in the treatment of cancer.

Synthesis, biological evaluation, and molecular modeling studies of novel heterocyclic compounds as anti-proliferative agents

Two novel series of heterocyclic compounds have been synthesized. In first series, isatin was allowed to react with substituted aromatic/cyclic carbonyl compounds to get desired mannich bases (2a-e). In second series, 4,5-disubstituted oxazoles (6a-p) wer

Potent, orally active heterocycle-based combretastatin A-4 analogues: Synthesis, structure - Activity relationship, pharmacokinetics, and in vivo antitumor activity evaluation

The synthesis and structure - activity relationship study of a series of compounds with heterocycles in place of the cis double bond in combretastatin A-4 (CA-4) are described. Substituted tosylmethyl isocyanides were found to be the key intermediates in construction of the heterocycles. Cytotoxicities of the heterocycle-based CA-4 analogues were evaluated against NCI-H460 and HCT-15 cancer cell lines. 3-Amino-4-methoxyphenyl and N-methyl-indol-5-yl were the best replacements for the 3-hydroxy-4-methoxyphenyl in CA-4. 4,5-Disubstituted imidazole was found to be the best for the replacement of the cis double bond in CA-4. Medicinal chemistry efforts led to the discovery of compounds 24h and 25f that were found to be 32 and 82% bioavailable, respectively, in rat. Evaluation of 24h and 25f against murine M5076 reticulum sarcoma in mice revealed that both compounds were orally efficacious with an increase in life span of 38.5 and 40.5%, respectively.