25274-38-8

Upstream product

• 5034-25-3 ent-10β,13-dihydroxy-3-oxo-20-norgibberella-1,6-diene-7,19-dioic acid 19,10β-lactone 7-methyl ester 
• 510-50-9 gibberellic acid methyl ester 
• 77-06-5 Gibberellic acid 
• 123972-87-2 O-Methyl (S)-prop-2-ynyl dithiocarbonate 
• 85622-93-1 temozolomide 
• 74-88-4 methyl iodide 
• 77-06-5 gibberellic acid 
• 77-78-1 dimethyl sulfate 
• 81010-90-4 C₂₉H₃₅BrO₈Si 
• 80994-37-2 C₂₉H₃₄O₈Si 
• 80994-36-1 C₂₅H₃₈O₇Si₂ 
• 22969-10-4 C₂₆H₄₀O₆Si₂ 
• 67-56-1 methanol 
• 186581-53-3 diazomethane 

Relevant academic research and scientific papers

Reaction of Methyl Gibberellate with Triphenylphosphine and Carbon Tetrachloride

Treatment of methyl gibberellate and its 3-epimer with triphenylphosphine and carbon tetrachloride containing acetone or pyridine, gave the 1β-chloro- and 1β,13-dichloro-Δ2-derivatives respectively as the major products.The 3-chloro-compounds were obtained as minor products.The 1-bromo-compounds were obtained with carbon tetrabromide.The structures of these compounds were established by location of the label in the products from methyl 3-epi-gibberellate.

Synthesis and anti-proliferative activity of allogibberic acid derivatives containing 1,2,3-triazole pharmacophore

Sixty novel allogibberic acid derivatives containing 1,2,3-triazole pharmacophore were designed and synthesized. The key chemical processes include aromatization of the A ring in gibberellins, formation of allogibberic azides and its copper mediated Huisgen 1,3-dipolar cycloaddition with alkynes. A number of hybrids containing α,β-unsaturated ketone moiety exhibited excellent in vitro cytotoxic activities. Some of the hybrids were more selective to MCF-7 and SW480 cell lines with IC50 values at least 8-fold more cytotoxic than cisplatin (DDP). The most potent compounds C43 and C45 are more cytotoxic than cisplatin (DDP) against all tested five tumor cell lines, with IC50 values of 0.25–1.72 μM. Mechanism of action studies indicated that allogibberic-triazole derivative C45 could induce the S phase cell cycle arrest and apoptosis in SMMC-7721 cell lines.

Imidazotetrazines as Weighable Diazomethane Surrogates for Esterifications and Cyclopropanations

Diazomethane is one of the most versatile reagents in organic synthesis, but its utility is limited by its hazardous nature. Although alternative methods exist to perform the unique chemistry of diazomethane, these suffer from diminished reactivity and/or correspondingly harsher conditions. Herein, we describe the repurposing of imidazotetrazines (such as temozolomide, TMZ, the standard of care for glioblastoma) for use as synthetic precursors of alkyl diazonium reagents. TMZ was employed to conduct esterifications and metal-catalyzed cyclopropanations, and results show that methyl ester formation from a wide variety of substrates is especially efficient and operationally simple. TMZ is a commercially available solid that is non-explosive and non-toxic, and should find broad utility as a replacement for diazomethane.

Synthesis of sesquiterpene-inspired derivatives designed for covalent binding and their inhibition of the NF-κB pathway

A significant portion of bioactive secondary metabolites are endowed with reactive functionalities that can engage in covalent interactions with their target. Sesquiterpene lactones in particular are rich in Michael acceptors that react with cysteines. Several polycyclic scaffolds derived from total synthesis or readily available polycyclic terpenes were used as the starting point in the synthesis of a library aiming to project mildly reactive functionalities (Michael acceptors or chloroacetates) with diverse geometries. Screening of the library for inhibition of the NF-κB pathway revealed several potent inhibitors that are chemically readily accessible.

EXPEDITIOUS SYNTHESIS OF GIBBERLLIN A5 AND ESTERS THEREOF

An expeditious synthesis of gibberellin A5 (GA5) esters is presented, from which GA5 may be prepared. The synthesis offers an inexpensive route of few steps to these compounds, starting from gibberellin A3 (GA3) esters in the presence of a metal hydride.

Unexpected C-arylation of a gibberellin: A cautionary note on the radical deoxygenation of homoallylic secondary alcohols

Aryl 3-O-thionocarbonates (7a-c), upon treatment with tributyltin hydride and a catalytic amount of AIBN in benzene at reflux, do not undergo deoxygenation as expected, but instead afford the 10-arylated bis-γ-lactones (8a-c) in high yields.

Highly Selective Epimerization of the 3β-Hydroxyl Function of Gibberellin Derivatives with a Base in an Aprotic Medium: Efficient Preparation of Methyl Esters of 3-epi-GA3 and 3-epi-GA1

Methyl esters of 3-epi-GA3 and 3-epi-GA1 were efficiently prepared from methyl esters of GA3 and GA1, respectively, by highly selective epimerization of the 3-hydroxyl function with a base in a low-polar aprotic medium.

Regio- und stereospezifische Addition von Diazomethan an Gibberellinsaeure: Ein neuer effektiver Weg zu 1,2-Methylengibberellinen

A new pathway to 1α,2α-methylenegibberellines via pyrazoline intermediates is reported.In contrast to the addition of diazomethane to the Δ1-double bond of corresponding enones in the case of 1 "Umpolung" of the regioselectivity with cis-addition from the α-side to give pyrazoline ester 4 is observed.Subsequent photolysis of 4 leads to the 1,2-cyclopropyl derivative 6.THe structure of the key compounds 4 and 6 are confirmed especially by n.m.r. and X-Ray analysis.

Substitution Reactions of the 3-Epimeric Methanesulphonates of Methyl Gibberellate

Whereas displacement of the 3β-(axial)-methylsulphonyloxy group from methyl gibberellate with lithium chloride or buffered aqueous acetone proceeds predominantly with syn rearrangement to afford the 1β-chloro- or 1β-hydroxy-gibberellin, the corresponding 3α-(equatorial) epimer reacts with simple inversion of configuration.This affords on the one hand a facile route to the 1-hydroxygibberellins and, on the other, a means of labelling gibberellins at C-3.