14447-01-9Relevant academic research and scientific papers
Traceless Release of Alcohols Using Thiol-Sensitive Oxanorbornadiene Linkers
Aioub, Allison G.,Higginson, Cody J.,Finn
, p. 3233 - 3236 (2018)
A class of ester-amide oxanorbornadiene (EA-OND) molecules was developed to release alcohol cargos by succinimide formation upon addition of a thiol reagent. The resulting ring-closed adducts undergo further fragmentation by retro-Diels-Alder reaction to release a furan moiety in a manner similar to oxanorbornadiene diesters. The rates of each of these fragmentation pathways in the same medium were found to be sensitive to the steric nature of the amide substituent. Alcohol release was much faster in protic solvents than in aprotic ones, suggesting that this system may be useful for rapid response to thiols in biological environments. Accordingly, the attachment and thiol-dependent release of cholesterol was characterized as an example of the manipulation of a drug-like cargo.
A novel fragmentation of 7-azabicyclo[2.2.1]hepta-2,5-dienes: Synthesis of cis-5-amidino-pyrrolidine-2-acetic acid derivatives
Weber, Dirk,Heller, Eberhard,Hoenke, Christoph,Hoerer, Stefan,Baeuerle, Peter,Austel, Volkhard
, p. 2357 - 2366 (2005)
A new fragmentation reaction of 3-bromo-7-azabicyclo[2.2.1]hepta-2,5-diene carboxylic esters with 2-amino or 2-aminomethyl anilines is described. It leads to cis-5-(benzimidazol-2-yl)- or cis-5-(3,4-dihydroquinazolin-2-yl)-pyrroline-2- acetic acid esters.
Synthesis and characterization of a new two photon excitable acid sphingomyelinase FRET probe
Mohamed, Zain H.,Rhein, Cosima,Schmid, Benjamin,Tripal, Philipp,Kornhuber, Johannes,Arenz, Christoph
, (2021)
Recently, FRET probes for acid sphingomyelinase (ASM) have enabled the observation of enzyme activity in intact cells for the first time. Here we present an ASM FRET probe specifically optimized for 2-photon excitation. To facilitate probe characterization and comparison to the previous probe, we mixed the two intact probes with defined amounts of the probes' ceramide cleavage products and mounted them on lipid beads. Directly excited NBD FRET acceptor fluorescene proved to be a useful means of reference and showed that the new probe is brighter, albeit only moderately, than the previous one. The new probe was then used to detect inhibition by various ASM inhibitors microscopically for the first time. Also in cells, directly excited acceptor fluorescence proved to be a useful parameter in addition to FRET to visualize inhibition of ASM.
Asymmetric synthesis of dihydrocarbazoles through a Friedel-Crafts alkylation/annulation sequential reaction of indoles
Hu, Linfeng,Cao, Weidi,Wang, Kaixuan,Liu, Xiaohua,Feng, Xiaoming
supporting information, p. 13138 - 13141 (2021/12/16)
An enantioselective tandem Friedel-Crafts alkylation/annulation of indoles with diazoacetoacetate enones is realized in one pot. A series of dihydrocarbazoles were obtained in moderate yields with good to excellent ee values by using a RhII/ScIII dual-metallic catalyst system. Control experiments revealed that ScIII is critical to both the alkylation and annulation.
Synthesis and evaluation of D-thioluciferin, a bioluminescent 6'-thio analog of Dluciferin
Rylands, Marwaan,Jardine, Anwar
, p. 176 - 189 (2021/03/17)
All known light-emitting firefly-bioluminescent luciferin analogs are either derived from the 6'-hydroxy- and/or 6'-aminoluciferin. We report the synthesis of D-thioluciferin, a 6'-thio analog or isostere of D-luciferin, starting from p-aminothiophenol, using a unique thioacrylate-S-protecting-group strategy. Upon treatment of Dthioluciferin with purified Photinus pyralis (Ppy) luciferase (Luc), a bioluminescence emission with a red-shift λmax relative to D-luciferin was observed. It was also shown that disulphide and sulphide analogs of Dthioluciferin did not produce similar bioluminescences relative to D-thioluciferin when treated with Ppy Luc under standard conditions, thus, providing a foundation for the development of D-thioluciferin based probes based on disulphide reduction and S-dealkylation.
Synthesis of carboxy-polyethylene glycol-amine (CA (PEG)n) and [1-14C]-CA (PEG)n via oxa-Michael addition of amino-polyethylene glycols to propiolates vs to acrylates
Song, Fengbin,Chen, Lu,Lin, Ronghui,Salter, Rhys
, p. 15 - 24 (2019/12/30)
Synthesis of carboxy-polyethylene glycol-amine (CA (PEG)n) via oxa-Michael addition of amino-polyethylene glycols to either acrylates or propiolates was investigated. Compared with the oxa-Michael addition to acrylates, the corresponding addition to propiolates was found to proceed under mild reaction conditions and afford the adducts in high yields from a broad scope of substrates. A two-step efficient and convenient synthesis of benzyl [1-14C]-propiolate from 14CO2 was therefore developed and utilized as a common synthon to afford practical and high yielding access to [1-14C]-CA (PEG)n.
Solvent-free and montmorillonite K10-catalyzed domino reactions for the synthesis of pyrazoles with alkynylester as a dual synthon
Annes, Sesuraj Babiola,Ramesh, Subburethinam,Saritha, Rajendhiran,Shankar, Bhaskaran,Subramanian, Saravanan
supporting information, p. 2388 - 2393 (2020/05/13)
A highly regioselective, solvent-free and montmorillonite K10 clay-catalyzed domino process with an unprecedented ring-closing C-C bond-formation reaction is described for the synthesis of a new class of 1,3,4-trisubstituted and 1,4-disubstituted pyrazole
Cyclopropanation of active methylene compounds with β-alkoxycarbonyl vinylsulfonium salts
Guo, Shenquan,Zhang, Niuniu,Tang, Xiangzheng,Mao, Zhifeng,Zhang, Xuejing,Yan, Ming,Xuan, Yining
supporting information, p. 406 - 408 (2018/09/25)
An efficient synthesis of β-alkoxycarbonyl vinylsulfonium salts had been developed. Their reaction with indene-1,3-diones and other active methylene compounds provided cyclopropane carboxylates in good yields. A tentative reaction mechanism was proposed.
DERIVATIVES OF LUCIFERIN AND METHODS FOR THEIR SYNTHESIS
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Page/Page column 31, (2019/02/13)
6-Thio derivatives of D-luciferin, also referred to as D-thioluciferins, having the general structure of Formula (I) are provided. Methods for synthesising D-luciferin, its derivatives, and their related 2-cyanobenzothiazole precursors are also provided. These compounds are commercially valuable due to their application in optical imaging, particularly in bioluminescence imaging.
Palladium-Catalyzed Regio- and Stereoselective Coupling-Addition of Propiolates with Arylsulfonyl Hydrazides: A Pattern for Difunctionalization of Alkynes
Liu, Lixin,Sun, Kang,Su, Lebin,Dong, Jianyu,Cheng, Lei,Zhu, Xiaodong,Au, Chak-Tong,Zhou, Yongbo,Yin, Shuang-Feng
supporting information, p. 4023 - 4027 (2018/07/15)
A new pattern for difunctionalization of alkynes via a palladium-catalyzed regio- and stereoselective coupling-addition of propiolates with arylsulfonyl hydrazides is disclosed. The approach enables the synthesis of various highly functionalized (E)-vinylsulfones in satisfactory yields. Arylsulfonyl hydrazides act as both aryl and sulfonyl sources via selective cleavage of Ar(C)-S and S-N bonds, which are simultaneously incorporated onto the terminal carbon atom of an alkyne molecule.
