116510-02-2Relevant academic research and scientific papers
Enediyne scaffold-based highly selective chemosensor for ratiometric sensing of H2PO4-ions
Ghosh, Kumaresh,Ali, Sk Sarfaraj,Joardar, Soumen
, p. 2054 - 2058 (2012)
Enediyne scaffold - based new chemosensor 1 has been designed and synthesized. The sensor 1 fluorometrically recognizes H2PO4- in CH3CN containing 1% DMSO by exhibiting a ratiometric change in emission upon complexation. The associat
Reduction-rebridging strategy for the preparation of ADPN-based antibody-drug conjugates
Koniev, Oleksandr,Dovgan, Igor,Renoux, Brigitte,Ehkirch, Anthony,Eberova, Jitka,Cianférani, Sarah,Kolodych, Sergii,Papot, Sébastien,Wagner, Alain
, p. 827 - 830 (2018)
The reduction-rebridging strategy is a powerful method for the preparation of stable and homogeneous antibody-drug conjugates (ADCs). In this communication, we describe the development of the arylene-dipropiolonitrile (ADPN) functional group for the rebri
Synthesis of crescent shaped heterocycle-fused aromatics via Garratt-Braverman cyclization and their DNA-binding studies
Ghosh, Debaki,Basu, Souradeep,Singha, Monisha,Das, Joyee,Bhattacharya, Prabuddha,Basak, Amit
, p. 2014 - 2018 (2017)
Three crescent shaped heterocycle-fused phenanthrene based systems 1–3 have been synthesized starting from benzene (or substituted benzene) 1,2-bis-propargyl alcohols. Bis-alkylation with propargylic bromides provided the key intermediate, the bis-propargyl bis-ethers. In spite of the possibility of many competing reactions, the latter underwent facile double Garratt-Braverman cyclization to provide compounds 1–3 in near quantitative yield, in a striking reaction involving the formation of four C–C bonds in a single step. Compounds 1–3 showed binding interaction with DNA, predominantly, via groove binding along with partial intercalation (combilexins). Molecular docking study supported the proposed binding modes.
Photoisomerization as a trigger for Bergman cyclization: Synthesis and reactivity of azoenediynes
Kar, Moumita,Basak, Amit,Bhattacharjee, Manish
, p. 5392 - 5396 (2005)
Cyclic enediynes 1a and 2a containing stable E-azo moiety (azoenediynes) have been synthesized. These compounds upon irradiation with long wavelength UV isomerize to the Z-compounds 1b and 2b, which can be thermally reisomerized to the Z compounds. Reacti
EMM-31 MATERIALS AND PROCESSES AND USES THEREOF
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Paragraph 0114; 0115, (2019/07/10)
The disclosure is related to EMM-31 materials, processes, and uses of the same as well as reagents used in the preparation of the EMM-31 materials, process and intermediates for preparing these reagents.
3-ARYL PROPIOLONITRILE COMPOUNDS FOR THIOL LABELING
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Paragraph 0290-0291, (2016/06/13)
The present invention relates to a process for labeling compounds comprising thiol moieties with 3-arylpropiolonitrile compounds, to 3-arylpropiolonitrile compounds substituted with tag moieties and to specific 3-arylpropiolonitrile linkers.
Synthesis and biological activity of new arenediyne-linked isoxazolidines
Romeo, Roberto,Navarra, Michele,Giofre, Salvatore V.,Carnovale, Caterina,Cirmi, Santa,Lanza, Giuseppe,Chiacchio, Maria A.
, p. 3379 - 3385 (2014/06/23)
Arenediyne-isoxazolidine conjugates have been synthesized as a new scaffold for the development of bioactive mimics. Some of the synthesized compounds are endowed with antiproliferative activity against three human cancer cell lines. Their thermal reactiv
Synthesis and reactivity of enediyne-nucleobase hybrids: Effect of intramolecular π-stacking
Roy, Snigdha,Bag, Subhendu Sekhar,Basak, Amit
supporting information, p. 8600 - 8611 (2012/10/29)
Three distinct classes of nucleobase-containing enediynes 1-9 with varying nature of the linker have been synthesized to explore the effect of π-stacking interaction in accelerating the rate of Bergman cyclization (BC). Chemical reactivity study, both experimental and computations demonstrated the important role that aromatic π-stacking interactions between the appended nucleobases within an enediyne frame play in lowering the activation barrier of Bergman cyclization.
Wolff rearrangement of β-alkynyl-α-diazo-β-ketoesters: Light-induced acetylene-allene isomerization and its use for activation of enediynes
Zhegalova, Natalia G.,Popik, Vladimir V.
experimental part, p. 969 - 975 (2012/01/13)
Irradiation of β-phenylethynyl-α-diazo-β-ketoester with 300 or 350nm light results in efficient and regioselective Wolff rearrangement producing only the product of alkynyl group migration. Addition of alcohols to the resulting α-oxoketene yields α-phenylethynyl-β-diester, which undergoes rapid (τ1min) tautomerization to 1,1-dicarbalkoxyallene. The latter then adds second molecule of alcohol in Michael fashion to form the final product, 2-(1-alkoxy-2-phenylvinyl)malonic ester. α-Phenylethynyl- β-ketoacid produced from the ketene in aqueous solutions does not isomerize to an allene but rather undergoes decarboxylation to give β,γ- acetylenic ester. Introduction of o-(3-hydroxy-1-propynyl) fragment in the structure of the parent α-diazo-β-ketoester allowed us to achieve two goals simultaneously: ring closure by intramolecular nucleophilic attack of propargyl alcohol on photo-generated ketene and the subsequent acetylene-allene rearrangement. The resulting enyne-allene undergoes spontaneous Myers-Saito cycloaromatization generating 1,4-biradical. In alcohol solutions, however, ketene reaction with solvent outcompetes the intramolecular process.
1,x-Elimination reactions: Extending the limits of a classical organic reaction
Werner, Christian,Hopf, Henning,Dix, Ina,Bubenitschek, Peter,Jones, Peter G.
, p. 9462 - 9477 (2008/12/22)
α,ω)-Dibromo derivatives in ich the two terminal carbon atom are separated by an unsaturated spacer unit (ππ spacer") undergo 1,x-elimination reactions (with x = 6, 8, 10, and 14), using Mori's reagent (nBu3SnSiMe3/CsF). The resulting cumulenic intermediates cyclodimerize in a subsequent step yielding novel macrocyclic acetylenic and bridged aromatic compounds (cyclophanes). Thus 1,6-eliminations were carried out with dibromide 17 to yield 1,3,7,9-cyclododecatetrayne (20) and with benzylbromide 24 to provide cyclophanes 26 and 27. By 1,8-eliminations the 16-membered macrocycle 33 could be prepared from enediyne 31, the benzannelated 1,5-cyclooctadiyne 41 from dibromide 38, and a mixture of cyclophanes 45 and 46 from the precursor 43. 1,10-Eliminations were carried out successfully with dibromides 47, 50, and 53 yielding the corresponding unsaturated cyclophanes ("cyclophynes") 49, 52, and 55. The influence of the solvent on the cyclodimerization 47→49 was investigated, with acetonitrile providing the highest yields. The heterophanes 59a and b were obtained by 1,10-elimination of the precursor dibromides 57 a and b, and in an elimination experiment involving a 1:1 mixture of the dibromides 50 and 57 b the "mixed dimer" 60 was isolated, besides the homodimers 52 and 59 b. The method reached its limits with the 1,14-elimination of 68, 70, and 74 providing the cyclophanes 69, 71, and 75 in varying amounts. Two final debrominations with 76 and 77, which in principle could undergo 1,16- and 1,20-eliminations reactions, respectively, failed. The structures of the new cyclophanes 49, 50, 59 a, and 59 b were established by X-ray structural analysis; all other structure assignments rest on the usual spectroscopic and analytical data.
