1462-75-5Relevant academic research and scientific papers
Titanium isopropoxide-mediated cis-selective synthesis of 3,4-substituted butyrolactones from CO2
Amaratunga, Angelo,Antico, Emanuele,Do, Cuong Dat,Hopmann, Kathrin H.,Mannisto, Jere K.,Repo, Timo,Sahari, Aleksi
supporting information, p. 3027 - 3030 (2022/03/14)
We report a Ti(OiPr)4-mediated multicomponent reaction, which produces 3,4-substituted cis-δ-lactones from alkyl magnesium chloride, benzaldehyde and CO2. The key intermediate, titanacyclopropane, is formed in situ from Ti(OiPr)4 and a Grignard reagent, which enables 1,2-dinucleophilic reactivity that is used to insert carbon dioxide and an aldehyde. An alternative reaction route is also described where a primary alkene is used to create the titanacyclopropane. A computational analysis of the elementary steps shows that the carbon dioxide and the aldehyde insertion proceeds through an inner-sphere mechanism. A variety of cis-butyrolactones can be synthesized with up to 7?:?1 diastereoselectivity and 77% yield.
Structure-Activity Relationship Studies of α-Ketoamides as Inhibitors of the Phospholipase A and Acyltransferase Enzyme Family
Zhou, Juan,Mock, Elliot D.,Al Ayed, Karol,Di, Xinyu,Kantae, Vasudev,Burggraaff, Lindsey,Stevens, Anna F.,Martella, Andrea,Mohr, Florian,Jiang, Ming,Van Der Wel, Tom,Wendel, Tiemen J.,Ofman, Tim P.,Tran, Yvonne,De Koster, Nicky,Van Westen, Gerard J.P.,Hankemeier, Thomas,Van Der Stelt, Mario
, p. 9340 - 9359 (2020/10/19)
The phospholipase A and acyltransferase (PLAAT) family of cysteine hydrolases consists of five members, which are involved in the Ca2+-independent production of N-acylphosphatidylethanolamines (NAPEs). NAPEs are lipid precursors for bioactive N-acylethanolamines (NAEs) that are involved in various physiological processes such as food intake, pain, inflammation, stress, and anxiety. Recently, we identified α-ketoamides as the first pan-active PLAAT inhibitor scaffold that reduced arachidonic acid levels in PLAAT3-overexpressing U2OS cells and in HepG2 cells. Here, we report the structure-activity relationships of the α-ketoamide series using activity-based protein profiling. This led to the identification of LEI-301, a nanomolar potent inhibitor for the PLAAT family members. LEI-301 reduced the NAE levels, including anandamide, in cells overexpressing PLAAT2 or PLAAT5. Collectively, LEI-301 may help to dissect the physiological role of the PLAATs.
Indolone derivative as well as preparation method and application thereof
-
Paragraph 0330-0333, (2019/07/04)
The invention relates to a compound represented by formula (A) or a pharmaceutically acceptable salt, a stereoisomer, a tautomer, a polymorphic substance, a solvate, a metabolite or a prodrug thereof,and also relates to a pharmaceutical composition containing the compound. The compound can be used for treating cancer or immune system diseases.
Controllable, Sequential, and Stereoselective C-H Allylic Alkylation of Alkenes
Qin, Ling,Sharique, Mohammed,Tambar, Uttam K.
supporting information, p. 17305 - 17313 (2019/11/03)
The direct conversion of C-H bonds into new C-C bonds represents a powerful approach to generate complex molecules from simple starting materials. However, a general and controllable method for the sequential conversion of a methyl group into a fully substituted carbon center remains a challenge. We report a new method for the selective and sequential replacement of three C-H bonds at the allylic position of propylene and other simple terminal alkenes with different carbon groups derived from Grignard reagents. A copper catalyst and electron-rich biaryl phosphine ligand facilitate the formation of allylic alkylation products in high branch selectivity. We also present conditions for the generation of enantioenriched allylic alkylation products in the presence of catalytic copper and a chiral phosphine ligand. With this approach, diverse and complex products with substituted carbon centers can be generated from simple and abundant feedstock chemicals.
Iron-Catalyzed Cross-Coupling of Alkynyl and Styrenyl Chlorides with Alkyl Grignard Reagents in Batch and Flow
Deng, Yuchao,Wei, Xiao-Jing,Wang, Xiao,Sun, Yuhan,No?l, Timothy
supporting information, p. 14532 - 14535 (2019/11/21)
Transition-metal-catalyzed cross-coupling chemistry can be regarded as one of the most powerful protocols to construct carbon–carbon bonds. While the field is still dominated by palladium catalysis, there is an increasing interest to develop protocols that utilize cheaper and more sustainable metal sources. Herein, we report a selective, practical, and fast iron-based cross-coupling reaction that enables the formation of Csp?Csp3 and Csp2?Csp3 bonds. In a telescoped flow process, the reaction can be combined with the Grignard reagent synthesis. Moreover, flow allows the use of a supporting ligand to be avoided without eroding the reaction selectivity.
Chromium(II)-Catalyzed Diastereoselective and Chemoselective Csp2-Csp3 Cross-Couplings Using Organomagnesium Reagents
Li, Jie,Ren, Qianyi,Cheng, Xinyi,Karaghiosoff, Konstantin,Knochel, Paul
supporting information, p. 18127 - 18135 (2019/11/19)
A simple protocol for performing chromium-catalyzed highly diastereoselective alkylations of arylmagnesium halides with cyclohexyl iodides at ambient temperature has been developed. Furthermore, this ligand-free CrCl2 enables efficient electrophilic alkenylations of primary, secondary, and tetiary alkylmagnesium halides with readily available alkenyl acetates. Moreover, this chemoselective C-C coupling reaction with stereodefined alkenyl acetates proceeds in a stereoretentive fashion. A wide range of functional groups on alkyl iodides and alkenyl acetates are well tolerated, thus furnishing functionalized Csp2-Csp3 coupling products in good yields and high diastereoselectivity. Detailed mechanistic studies suggest that the in situ generated low-valent chromium(I) species might be the active catalyst for these Csp2-Csp3 cross-couplings.
A Short Access to Symmetrically α,α-Disubstituted α-Amino Acids from Acyl Cyanohydrins
Boukattaya, Fatma,Caillé, Julien,Ammar, Houcine,Rouzier, Florian,Boeda, Fabien,Pearson-Long, Morwenna S. M.,Bertus, Philippe
, p. 906 - 916 (2016/03/12)
A straightforward synthesis of symmetrically α,α-disubstituted α-amino acids is presented. The key step of this process relies on the efficient double addition of Grignard reagents to acyl cyanohydrins to provide N-acyl amino alcohols selectively in good yields. The chemoselectivity of the reaction was modulated by the nature of the acyl moiety. Eleven amino acids were prepared, including the particularly simple divinylglycine, which is not easily accessible by using conventional methods.
Heterocyclic aromatic compounds useful as growth hormone secretagogues
-
Page/Page column 16, (2010/10/20)
Novel heterocyclic aromatic compounds are provided that are useful in stimulating endogenous production or release of growth hormone, said compounds having the general structure of formula I wherein R1, R1a, R6, Xa/s
Synthesis of η-arene derivatives of chromium and molybdenum containing Lewis-acid boron substituents
Green, Malcolm L. H.,Wagner, Matthias
, p. 2467 - 2473 (2007/10/03)
The compounds Ph(CH2)3B(OH)2 I, [Ph(CH2)3BO]3 II, Ph(CH2)3B(1,2-O2C6H4) III, Ph(CH2)3BC8H14 IV (BC8H14 = 9-borabicyclo[3.3.1]nonan-9-yl), [Cr{η-Ph(CH2)3B(1,2-O2C6H 4)}(CO)3] 1, [Cr{η-Ph(CH2)3BC8H14}(CO) 3] 2, [Cr{η-Ph(CH2)3BBr2·SMe 2}(CO)3] 3, [Cr{η-Ph(CH2)4BC8H14}(CO) 3] 4, [Cr(η-Ph(CH2)4BC8H14}(CO) 2(PPh3)] 5, [Cr{η-PhCH2CH=CH2}(CO)3] 6, [Cr{η-Ph(CH2)2CH=CH2}(CO)3] 7, [Cr{η-Ph(CH2)2η-CH=CH2}(CO) 2] 8, [Cr{η-Ph(CH2)2CH=CH2}(CO) 2(PPh3)] 9, [Li(Et2O)n][Cr{η-PhCH2CH=CH 2}(CO)2{C(O)Ph}] 10, [Li(Et2O)n][Cr{η-Ph(CH2) 2CH=CH2}(CO)2{C(O)Ph}] 11, [Mo{η-Ph(CH2)3BC8H14} 2] 12 and [Cr{η-Ph(CH2)3BOC8H14}(CO) 3] 13, have been prepared and characterised. Compounds 1-5, 12 and 13 have π-donor η-arene ligands which also bear a Lewis-acid α-acceptor boron group. There was no evidence that these boron groups formed ground-state intra- or inter-molecular interactions with the Lewis base functions of the carbonyl oxygen atoms.
Quinoline ether alkanoic acids
-
, (2008/06/13)
Compounds having the formula: STR1 are inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating diarrhea, hypertension, angina, platelet aggregation, cerebral spasm, premature labor, spontaneous abortion, dysmenorrhea, and migraine.
