scholarly journals “Free of Base” Sulfa-Michael Addition for Novel o-Carboranyl-DL-Cysteine Synthesis

Crystals ◽  
2020 ◽  
Vol 10 (12) ◽  
pp. 1133
Author(s):  
Julia Laskova ◽  
Irina Kosenko ◽  
Ivan Ananyev ◽  
Marina Stogniy ◽  
Igor Sivaev ◽  
...  
Keyword(s):  
Michael Addition ◽  
Addition Reaction ◽  
Neutron Capture Therapy ◽  
Michael Addition Reaction ◽  
X Ray Diffraction ◽  
Deuterium Label ◽  
X Ray ◽  
Boron Neutron Capture ◽  
Cysteine Synthesis ◽  
Base Method

The sulfa-Michael addition reaction was applied for the two-step synthesis of o-carboranyl cysteine 1-HOOCCH(NH2)CH2S-1,2-C2B10H11 from the trimethylammonium salt of 1-mercapto-o-carborane and methyl 2-acetamidoacrylate. To avoid the decapitation of o-carborane into its nido-form, the “free of base” method under mild conditions in a system of two immiscible solvents toluene-H2O was developed. The replacement of H2O by 2H2O resulted in carboranyl-cysteine containing a deuterium label at the α-position of the amino acid 1-HOOCCD(NH2)CH2S-1,2-C2B10H11. The structure of the protected o-carboranyl cysteine was determined by single-crystal X-ray diffraction. The obtained compounds can be considered as potential agents for the Boron Neutron Capture Therapy of cancer.

scholarly journals Synthesis of Zwitter-Ionic Conjugate of Nido-Carborane with Cholesterol

Molecules ◽  
2021 ◽  
Vol 26 (21) ◽  
pp. 6687
Author(s):  
Anna A. Druzina ◽  
Olga B. Zhidkova ◽  
Nadezhda V. Dudarova ◽  
Natalia A. Nekrasova ◽  
Kyrill Yu. Suponitsky ◽  
...  
Keyword(s):  
Molecular Structure ◽  
Neutron Capture ◽  
Neutron Capture Therapy ◽  
Terminal Alkyne ◽  
X Ray Diffraction ◽  
Dimethylamino Group ◽  
X Ray ◽  
Boron Neutron Capture ◽  
Carborane Derivative ◽  
A Charge

9-HC≡CCH2Me2N-nido-7,8-C2B9H11, a previously described carboranyl terminal alkyne, was used for the copper(I)-catalyzed azide-alkyne cycloaddition with azido-3β-cholesterol to form a novel zwitter-ionic conjugate of nido-carborane with cholesterol, bearing a 1,2,3-triazol fragment. The conjugate of nido-carborane with cholesterol, containing a charge-compensated group in the linker, can be used as a precursor for the preparation of liposomes for BNCT (Boron Neutron Capture Therapy). The solid-state molecular structure of a nido-carborane derivative with the 9-Me2N(CH2)2Me2N-nido-7,8-C2B9H11 terminal dimethylamino group was determined by single-crystal X-ray diffraction.

Catalyst-Free One-Pot Synthesis of Chromeno-Imidazo-Pyridinones by an Aza-Michael Addition/Rearrangement/Heterocyclization Tandem Reaction

Synlett ◽  
2018 ◽  
Vol 29 (11) ◽  
pp. 1437-1440 ◽  
Author(s):  
Oualid Talhi ◽  
Norah Bennamane ◽  
Artur Silva ◽  
Houria Lakhdari ◽  
Ridha Hassaine ◽  
...  
Keyword(s):  
Michael Addition ◽  
Room Temperature ◽  
Addition Reaction ◽  
2D Nmr ◽  
X Ray Diffraction ◽  
One Pot ◽  
X Ray ◽  
Catalyst Free ◽  
One Pot Synthesis ◽  
New Compounds

A one-pot synthesis of a novel series of chromeno-imidazo-pyridinone derivatives from 3-[(2-hydroxyphenyl)-3-oxoprop-1-en-1-yl]chromones and ethane-1,2-diamine at room temperature under catalyst-free conditions has been successfully developed. This approach involves a tandem aza-Michael addition reaction, a chromone-to-chromanone rearrangement, and a heterocyclization sequence, leading to chromeno-imidazo-pyridinone polyheterocycles. The structure and absolute configurations of the new compounds were elucidated by a combination of 1D- and 2D-NMR analyses and single-crystal X-ray diffraction.

An Efficient One-Step Synthesis of Dihydroquinoline and Its Application as a Fluorescence Sensor for Selective Detection of Copper (II)

Synthesis ◽  
2018 ◽  
Vol 50 (19) ◽  
pp. 3886-3890 ◽  
Author(s):  
Anawat Ajavakom ◽  
Kamrul Hassan ◽  
Lamduan Jonsai ◽  
Pawitporn Sittapairoj ◽  
Vachiraporn Ajavakom ◽  
...  
Keyword(s):  
Detection Limit ◽  
Fluorescence Quenching ◽  
Addition Reaction ◽  
Selective Detection ◽  
Michael Addition Reaction ◽  
X Ray Diffraction ◽  
X Ray ◽  
Methyl Propiolate ◽  
Amino Phenol ◽  
One Step

An efficient one-step synthetic pathway to dihydroquinoline (DHQ) and benzodihydroquinoline (BDHQ) derivatives involving 1,2-Michael addition reaction between amino phenol/naphthol and two molecules of methyl propiolate followed by intramolecular cyclization and aromatization using cuprous iodide as a catalyst was successfully developed. The synthesized DHQ derivatives displayed highly selective fluorescence quenching in the presence of copper(II) with a very low detection limit (LOD for DHQ is 0.20 μM). Moreover, the mechanisms of both formation of the corresponding DHQ and the fluorescence quenching by copper(II) are proposed along with the evidence of X-ray diffraction data.

scholarly journals Synthesis and Structure of Nido-Carboranyl Azide and Its “Click” Reactions

Molecules ◽  
2021 ◽  
Vol 26 (3) ◽  
pp. 530
Author(s):  
Anna A. Druzina ◽  
Olga B. Zhidkova ◽  
Nadezhda V. Dudarova ◽  
Irina D. Kosenko ◽  
Ivan V. Ananyev ◽  
...  
Keyword(s):  
Molecular Structure ◽  
Neutron Capture ◽  
Cluster Compounds ◽  
Neutron Capture Therapy ◽  
Terminal Alkynes ◽  
X Ray Diffraction ◽  
Click Reactions ◽  
X Ray ◽  
Boron Neutron Capture ◽  
Cobalt Iron

Novel zwitter-ionic nido-carboranyl azide 9-N3(CH2)3Me2N-nido-7,8-C2B9H11 was prepared by the reaction of 9-Cl(CH2)3Me2N-nido-7,8-C2B9H11 with NaN3. The solid-state molecular structure of nido-carboranyl azide was determined by single-crystal X-ray diffraction. 9-N3(CH2)3Me2N-nido-7,8-C2B9H11 was used for the copper(I)-catalyzed azide-alkyne cycloaddition with phenylacetylene, alkynyl-3β-cholesterol and cobalt/iron bis(dicarbollide) terminal alkynes to form the target 1,2,3-triazoles. The nido-carborane-cholesterol conjugate 9-3β-Chol-O(CH2)C-CH-N3(CH2)3Me2N-nido-7,8-C2B9H11 with charge-compensated group in a linker can be used as a precursor for preparation of liposomes for Boron Neutron Capture Therapy (BNCT). A series of novel zwitter-ionic boron-enriched cluster compounds bearing a 1,2,3-triazol-metallacarborane-carborane conjugated system was synthesized. Prepared conjugates contain a large amount of boron atom in the biomolecule and potentially can be used for BNCT.

Cupin Variants as Macromolecular Ligand Library for Stereoselective Michael Addition of Nitroalkanes

2019 ◽  
Author(s):  
Nobutaka Fujieda ◽  
Miho Yuasa ◽  
Yosuke Nishikawa ◽  
Genji Kurisu ◽  
Shinobu Itoh ◽  
...  
Keyword(s):  
Michael Addition ◽  
In Silico ◽  
Addition Reaction ◽  
Single Point ◽  
Point Mutations ◽  
Unsaturated Ketone ◽  
Michael Addition Reaction ◽  
Beta Barrel ◽  
Cupin Superfamily ◽  
Single Point Mutations

Cupin superfamily proteins (TM1459) work as a macromolecular ligand framework with a double-stranded beta-barrel structure ligating to a Cu ion through histidine side chains. Variegating the first coordination sphere of TM1459 revealed that H52A and H54A/H58A mutants effectively catalyzed the diastereo- and enantio-selective Michael addition reaction of nitroalkanes to an α,β-unsaturated ketone. Moreover, in silico substrate docking signified C106N and F104W single-point mutations, which inverted the diastereoselectivity of H52A and further improved the stereoselectivity of H54A/H58A, respectively.

Tandem Alkylation/Michael Addition Reaction of Dithiocarbamic Acids with Alkyl γ-Bromocrotonates: Access to Functionalized 1,3-Thiazolidine-2-thiones

Synthesis ◽  
2021 ◽  
Author(s):  
Azim Ziyaei Halimehjani ◽  
Petr Beier ◽  
Maryam Khalili Foumeshi ◽  
Ali Alaei ◽  
Blanka Klepetářová
Keyword(s):  
Amino Acids ◽  
Carbon Disulfide ◽  
Multicomponent Reaction ◽  
Michael Addition ◽  
Addition Reaction ◽  
Primary Amines ◽  
Oxidation Reactions ◽  
Michael Addition Reaction ◽  
Synthetic Utility ◽  
Reaction Proceeds

AbstractThiazolidine-2-thiones were prepared via a novel multicomponent reaction of primary amines (amino acids), carbon disulfide, and γ-bromocrotonates. The reaction proceeds via a domino alkylation/intramolecular Michael addition to provide the corresponding thiazolidine-2-thiones in high to excellent yields. By using diamines in this protocol, bis(thiazolidine-2-thiones) derivatives were synthesized. The synthetic utility of the adducts was demonstrated by hydrolysis, amidation, and oxidation reactions.

Bisphosphine catalyzed sequential [3 + 2] cycloaddition and Michael addition of ynones with benzylidenepyrazolones via dual α′,α′-C(sp3)–H bifunctionalization to construct cyclopentanone-fused spiro-pyrazolones

2018 ◽  
Vol 16 (48) ◽  
pp. 9461-9471 ◽  
Author(s):  
Jiayong Zhang ◽  
Zhiwei Miao
Keyword(s):  
Michael Addition ◽  
Addition Reaction ◽  
Michael Addition Reaction

A sequential [3 + 2] cycloaddition and Michael addition reaction of ynones with benzylidenepyrazolones afforded cyclopentanone-fused spiro-pyrazolones catalyzed by DPPB via dual α′,α′-C(sp3)–H bifunctionalization.

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