Methyl Azidoacetate Research Articles

Synthesis, Characterization and Biological Evaluation of Novel Dihydropyranoindoles Improving the Anticancer Effects of HDAC Inhibitors.

The dihydropyranoindole scaffold was identified as a promising target for improving the anti-cancer activity of HDAC inhibitors from the preliminary screening of a library of compounds. A suitable methodology has been developed for the preparation of novel dihydropyranoindoles via the Hemetsberger indole synthesis using azido-phenylacrylates, derived from the reaction of corresponding alkynyl-benzaldehydes with methyl azidoacetate, followed by thermal cyclization in high boiling solvents. Anti-cancer activity of all the newly synthesized compounds was evaluated against the SH-SY5Y and Kelly neuroblastoma cells as well as the MDA-MB-231 and MCF-7 breast adenocarcinoma cell lines. Biological studies showed that the tetracyclic systems had significant cytotoxic activity at higher concentration against the neuroblastoma cancer cells. More importantly, these systems, at the lower concentration, considerably enhanced the SAHA toxicity. In addition to that, the toxicity of designated systems on the healthy human cells was found to be significantly less than the cancer cells.

Synthesis of 1,4-disubstituted 1,2,3-triazoles based on cobalt bis(1,2-dicarbollide)

An approach to the synthesis of new 1,4-disubstituted 1,2,3-triazoles, in which one or both substituents contain the cobalt bis(1,2-dicarbollide) fragment, was suggested based on the 1,3-dipolar cycloaddition of azides to alkynes catalyzed by copper(I) compounds. The reaction of cobalt bis(1,2-dicarbollide) azido derivatives with different terminal acetylenes led to 1,2,3-triazoles with the [((CH2)2X(CH2)2O-C2B9H10)Co(C2B9H11)] (X = O or CH2) substituent at position 1 and the organic substituent at position 4. The [3+2] cycloaddition reaction of cobalt bis(1,2-dicarbollide) alkynyl derivatives with methyl azidoacetate furnished isomeric 1,4-disubstituted 1,2,3-triazoles with the metallacarborane fragment at position 4. 1,2,3-Triazole with metallacarborane substituents at positions 1 and 4 containing 36 boron atoms was also synthesized.

Sonochemical Synthesis of Closed [5,6]-bridged Aziridino[70]fullerene Derivative and Self-assembled Multilayer Films

This cycloaddition of [70]fullerene with methyl azidoacetate in benzene under ultrasonic irradiated condition afforded the closed [5,6]-bridged aziridino[70]fullerene derivative, which was unusual product of cycloaddition to the 5,6-junction of fullerene. Its structure was determined by FAB-MS, UV-vis, <TEX>$^1H-$</TEX> and <TEX>$^{13}C$</TEX>-NMR spectral data. The closed [5,6]-bridged aziridino[70]fullerene-functionalized gold nanoparticle films were self-assembled using the layer-by-layer method on the reactive of glass slides functionalized with 3-mercaptopropyl trimethoxysilane. The functionalized glass slides were alternately soaked in the solution containing closed the [5,6]-bridged aziridino[70]fullerene and 4-aminothiophenoxide/hexanethiolate-protected gold nanoparticles. The closed [5,6]-bridged aziridino[70]fullerene-functionalized gold nanoparticle films have grown up to 5 layers depending on the immersion time. The self-assembled nanoparticle multilayer films were characterized using UV-vis spectroscopy showed that the surface plasmon band of gold at 527 nm gradually became more evident as successive layers were added to the films.

Reactions of Furo[2,3-b]pyrrole and Furo[3,2-b]pyrrole-Type Aldehydes

The synthesis of methyl 2-formyl-6-(methoxymethyl)furo[2,3-b]pyrrole-5-carboxylate (1d) is described. The reactions of methyl 2-formylfuro[2,3-b]pyrrole-5-carboxylates 1a-1d with malononitrile afforded methyl 2-(2,2-dicyanovinyl)furo[2,3-b]pyrrole-5-carboxylates 3a-3d, with methyl cyanoacetate methyl 2-[2-cyano-2-(methoxycarbonyl)vinyl]furo[2,3-b]pyrrole-5-carboxylates 4a-4d and with 2-furylacetonitrile methyl 2-[2-cyano-2-(2-furyl)vinyl]furo[2,3-b]pyrrole-5-carboxylates 5a-5d. Compounds 1b-1d and methyl azidoacetate gave the appropriate vinylazides 6b-6d, which were used for preparation of substituted furo[2,3-b:4,5-b']dipyrroles 7b-7d. Reactivity of furo[2,3-b]pyrrole aldehydes 1a-1d and furo[3,2-b]pyrrole aldehydes 2a-2c in their reactions with 5,5-dimethylcyclohexane-1,3-dione is compared. The prepared methyl 2-[bis(4,4-dimethyl-2,6-dioxocyclohexyl)methylfuro[2,3-b]pyrrole-5-carboxylates 8a-8d and their isomers 10a-10c cyclized into substituted octahydroxanthenes 9a-9d and 11a-11c, respectively. Methyl 4-benzyl-2- [(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)methyl]furo[3,2-b]pyrrole-5-carboxylate (12) was prepared using microwave irradiations.

ChemInform Abstract: Reactions of Thioketones with Methyl Azidoacetate.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform Abstract: Methoxide Ion Mediated Reactions of Methyl Azidoacetate with 4‐ and 2‐ Cyanobenzaldehyde. An Unexpected Cyclization of the ortho Isomer to a 2(1H)‐Benzazepine Derivative.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Methoxide ion mediated reactions of methyl azidoacetate with 4‐and 2‐cyanobenzaldehyde. An unexpected cyclization of the ortho isomer to a 2(1H)‐benzazepine derivative

AbstractA condensation reaction of 4‐cyanobenzaldehyde (1) with methyl azidoacetate (2) in the presence of sodium methoxide produces a mixture of geometrical isomers of azidocinnamates 3 which undergoes thermolysis to give an indole 4. By contrast, the treatment of 2‐cyanobenzaldehyde (5) with 2 in the presence of sodium methoxide and followed by the usual workup furnishes an azepine derivative 6.

ChemInform Abstract: Synthesis and Analgesic Evaluation of 4‐(2‐Heptyloxy)‐7‐((Z)‐(3‐hydroxycyclohexyl))indole: A Caveat on Indole‐Phenol Bioisosterism.

AbstractThe aldehyde (Ia) is etherified to (Ib) and then coupled with methyl azidoacetate (III) to yield the azidoester (IV) which cyclizes, forming the indole (Va).

Vinyl azides in heterocyclic synthesis. Part 7. Synthetic studies on the cytotoxic marine alkaloid amphimedine

In an approach to the synthesis of the pentacyclic alkaloid amphimedine (1), a key tetracyclic structure (6) is readily constructed from 2-methoxyacridine-9-carbaldehyde in three steps. Condensation of the aldehyde (2) with methyl azidoacetate gives the vinyl azide (3) which on thermolysis in xylene gives the pyridoacridines (4) and (5) in high yield (78% and 19% respectively); this represents the first cyclisation of a vinyl nitrene to a peri-position. Oxidation of the major pyridoacridine (4), or of the mixed pyridoacridines (4) and (5), with manganese dioxide gives the pyridoacridone (6), but neither (6) nor the analogous isopropyl ester (9) undergoes Diels–Alder reaction with the azadiene (7).

A general method for the synthesis of 2-arylpyrroles

Reaction of methyl azidoacetate with β-arylacroleins, followed by cyclisation of the obtained derivatives easily leads to arylpyrroles. N M R and mass spectra data are given and the Vilsmeier formylation of some arylpyrroles is described.