1078-72-4

Upstream product

• 19501-58-7 4-methoxyphenylhydrazine hydrochloride 
• 67-64-1 acetone 

Downstream Products

• 1076-74-0 5-methoxy-2-methyl-1H-indole 
• 133902-76-8 4-acetyl-1-(4-methoxyphenyl)-3,3-dimethyl-1,2,4-triazolidin-5-one 
• 131366-30-8 2-(4-Methoxy-phenyl)-5,5-dimethyl-[1,2,4]triazolidin-3-one 
• 105122-14-3 C₁₁H₁₄N₃O₂⁽¹⁺⁾*BF₄^(1-) 
• 105122-06-3 (1-Isocyanato-1-methyl-ethyl)-(4-methoxy-phenyl)-diazene 
• 22863-27-0 1-(4-methoxyphenyl)-3-methyl-1,2,4-triazolin-5-one 

Relevant academic research and scientific papers

One-pot synthesis of an indole-substituted 7,8-dicarba-nido-dodecahydroundecaborate(-1)

Carbaboranes are increasingly used as pharmacophores to replace phenyl substituents in established drug molecules. In contrast to traditional organic chemistry, elaborate procedures to introduce functionality frequently fail in the case of carbaboranes and their chemistry is often hampered by degradation of the cluster. Herein, the development of a one-pot synthesis of a water-soluble N-nido-dicarbaborato indole is presented, including a proposed mechanism for the reaction sequence. These studies provide useful synthetic tools for the conjugation of two important pharmacophores, indoles and carbaboranes. This journal is

Autoxidation of hydrazones. Some new insights

(Chemical Equation Presented) Autoxidation of hydrazones is a generally occurring reaction, leading mostly to the formation of α- azohydroperoxides. All structural kinds of hydrazones, having at least one hydrogen atom on nitrogen, are prone to autoxidation; however, there are marked differences in the rate of the reaction. Hydrazones of aliphatic ketones are 1-2 orders of magnitude more reactive than analogous derivatives of aromatic ketones. Even less reactive are the hydrazones of chalcones, which function also as efficient inhibitors of autoxidation of other hydrazones. These differences can be attributed to the reduction of the rate of the addition of oxygen to a hydrazonyl radical, which is a reversible reaction. In the case of conjugated ketones, it becomes endothermic, making this elementary step slow down and the chain termination reactions become important. Substituents influence the stability of hydrazonyl radicals and, consequently, the bond dissociation energies of the N-H bonds. In acetophenone phenylhydrazones, the substituents placed on the ring of hydrazine moiety exhibit a higher effect (Hammett ρ = -2.8) than those on the ketone moiety (ρ = -0.82), which denotes higher importance of the structure with spin density concentrated on nitrogen in delocalized hydrazonyl radical. Electronic effects of the substituents also affect the transition state for the abstraction of hydrogen atom by electrophilic peroxy radicals; NBO analysis display a negative charge transfer of about 0.4 eu from hydrazone to a peroxy radical in the transition state.

Inhibition of cytosolic phospholipase A2α: Hit to lead optimization

Compound 1 was previously reported to be a potent inhibitor of cPLA 2α in both artificial monomeric substrate and cell-based assays. However, 1 was inactive in whole blood assays previously used to characterize cyclooxygenase and lipoxygenase inhibitors. The IC50 of 1 increased dramatically with cell number or lipid/detergent concentration. In an attempt to insert an electrophilic ketone between the indole and benzole acid moieties, we discovered that increasing the distance between the two moieties gave a compound with activity in the GLU (7-hydroxycoumarinyl-γ- linolenate) micelle assay, which contains lipid and detergent. Extensive structure-activity relationship work around this lead identified a potent pharmacophore for cPLA2α inhibition. The IC50s between the GLU micelle and rat whole blood assays correlated highly. No correlation was found for other parameters, including lipophilicity or acidity of the required acid functionality. Compounds 25, 39, and 94 emerged as potent, selective inhibitors of cPLA2α and represent well-validated starting points for further optimization.

Method of controlling plant growth

A method of controlling plant growth wherein the plant or its seed are treated with thiazolyl-indolyl compounds.