166170-71-4Relevant academic research and scientific papers
Sulfonium ion-promoted traceless Schmidt reaction of alkyl azides
Ardiansah, Bayu,Kakiuchi, Kiyomi,Morimoto, Tsumoru,Tanimoto, Hiroki,Tomohiro, Takenori
supporting information, p. 8738 - 8741 (2021/09/08)
Schmidt reaction by sulfonium ions is described. General primary, secondary, and tertiary alkyl azides were converted to the corresponding carbonyl or imine compounds without any trace of the activators. This bond scission reaction through 1,2-migration of C-H and C-C bonds was accessible to the one-pot substitution reaction.
Total Synthesis of the Proposed Structure of Penasulfate A: L -Arabinose as a Source of Chirality
Gao, Yangguang,Cao, Zhou,Zhang, Qiang,Guo, Rui,Ding, Fei,You, Qingliang,Bi, Jingjing,Zhang, Yongmin
, p. 1908 - 1916 (2019/08/20)
The total synthesis of putative penasulfate A was effectively achieved by a convergent strategy with a longest linear sequence of 14 steps and overall yield of 8.6%. The highlights of our strategy involved an E-selective olefin cross-metathesis, Suzuki cross-coupling, and a copper(I)-catalyzed coupling reaction.
A natural ɑ - glucosidase inhibitor Penasulfate A synthetic method (by machine translation)
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Paragraph 0029; 0040; 0041, (2019/02/04)
The invention provides a natural ɑ - glucosidase inhibitor Penasulfate A synthetic method, including by the 1, 12 - dodecanediol via 5 step synthesis 12 - thirteen carbon olefine acid, L - arabinose via the 3 step synthesis (2 S, 3 R) - 2, 3 - oxygen - isopropyl - 4 - pentene - 1, 2, 3 - triol, (S)- Roche ester via the 8 step synthesis of chiral methyl undecenyl fundamental frequency that mellow boron ester, 12 - thirteen alkenylene acid and (2 S, 3 R) - 2, 3 - oxygen - isopropyl - 4 - pentene - 1, 2, 3 - triol in GrubbsII catalyst under the action of the olefin metathesis reaction, and then with the (R)- piperidine - 2 - carboxylic acid methyl ester reaction to prepare amide, re-oxidation results in the aldehyde, Takai alkene alkylation by thirteen alkenylene iodide, with the insecticidal compositions of the fundamental frequency that chiral methyl mellow boron ester in Pd (PPh3 )4 Catalytic, ethyl alcohol thallium as alkali under the condition of the key Suzuki coupling, hydrogenation reduction, [...], sulfuric acid ester, shall Penasulfate A. The present invention provides natural product Penasulfate A throughout the synthetic route for the first time, the olefin metathesis reactions and Suzuki coupling as a key reaction, the line is comparatively simple high efficiency, a high degree of convergence, the operation is easy to grasp. (by machine translation)
Development of Hybrid Phospholipid Mimics as Effective Agonists for Liver Receptor Homologue-1
Flynn, Autumn R.,Mays, Suzanne G.,Ortlund, Eric A.,Jui, Nathan T.
supporting information, p. 1051 - 1056 (2018/09/21)
The orphan nuclear receptor Liver Receptor Homologue-1 (LRH-1) is an emerging drug target for metabolic disorders. The most effective known LRH-1 modulators are phospholipids or synthetic hexahydropentalene compounds. While both classes have micromolar ef
Bongkrekic Acid Analogue, Lacking One of the Carboxylic Groups of its Parent Compound, Shows Moderate but pH-insensitive Inhibitory Effects on the Mitochondrial ADP/ATP Carrier
Yamamoto, Atsushi,Hasui, Keisuke,Matsuo, Hiroshi,Okuda, Katsuhiro,Abe, Masato,Matsumoto, Kenji,Harada, Kazuki,Yoshimura, Yuya,Yamamoto, Takenori,Ohkura, Kazuto,Shindo, Mitsuru,Shinohara, Yasuo
, p. 1304 - 1322 (2015/10/28)
Bongkrekic acid, isolated from Burkholderia cocovenenans, is known to specifically inhibit the mitochondrial ADP/ATP carrier. However, the manner of its interaction with the carrier remains elusive. In this study, we tested the inhibitory effects of 17 bo
Synthesis of long-chain fatty acid derivatives as a novel anti-Alzheimer's agent
Zhang, Hong-Yan,Yamakawa, Yu-Ichiro,Matsuya, Yuji,Toyooka, Naoki,Tohda, Chihiro,Awale, Suresh,Li, Feng,Kadota, Shigetoshi,Tezuka, Yasuhiro
, p. 604 - 608 (2014/01/23)
In order to develop new drugs for Alzheimer's disease, we prepared 17 fatty acid derivatives with different chain lengths and different numbers and positions of double bonds by using Wittig reaction and stereospecific hydrogenation of triple bonds as key reactions. Among them, (4Z,15Z)- octadecadienoic acid (10) and (23Z,34Z)-heptatriacontadienoic acid (16) showed the most potent neurite outgrowth activities on Aβ(25-35)-treated rat cortical neurons, which activities were comparable to that of a positive control, NGF. Both fatty acids 10 and 16 possess two (Z)-double bonds at the n-3 and n-14 positions, which might be important for the neurite outgrowth activity.
Molecular design, synthesis, and evaluation of novel potent apoptosis inhibitors inspired from bongkrekic acid
Okuda, Katsuhiro,Hasui, Keisuke,Abe, Masato,Matsumoto, Kenji,Shindo, Mitsuru
, p. 2253 - 2260 (2013/01/15)
Bongkrekic acid (BKA) is an inhibitor of adenine nucleotide translocase (ANT). Since inhibition of ANT is connected to the inhibition of cytochrome c release from mitochondria, which then results in the suppression of apoptosis, it has been used as a tool for the mechanistic investigation of apoptosis. BKA consists of a long carbon chain with two asymmetric centers, a nonconjugated olefin, two conjugated dienes, three methyl groups, a methoxyl group, and three carboxylic acids. This complicated chemical structure has caused difficulties in synthesis, supply, and biochemical mechanistic investigations. In this study, we designed and synthesized more simple tricarboxylic acids that were inspired by the molecular structure of BKA. Their cytotoxicity and apoptosis-preventing activity in HeLa cells and the effect on the mitochondrial inner membrane potential (Δψm) in HL-60 cells were then evaluated. All tested tricarboxylic acid derivatives including BKA showed little toxicity against HeLa cells. BKA and two of the synthesized derivatives significantly suppressed staurosporine (STS)-induced reductions in cell viability. Furthermore, STS-induced Δψm collapse was significantly restored by pretreatment with BKA and a tricarboxylic acid derivative. Other derivatives, in which one of three carboxylic acids was esterified, exhibited potent toxicity, especially a derivative bearing a carbon chain of the same length as that of BKA. In conclusion, we have developed a new lead compound as an apoptosis inhibitor bearing three carboxylic acids connected with the proper length of a long carbon chain.
Polyoxazolines with Inert Terminating Groups, Polyoxazolines Prepared from Protected Initiating Groups and Related Compounds
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, (2011/06/19)
The present disclosure provides novel functional polyoxazoline derivatives prepared by terminating polyoxazoline polymerization with inert chemical groups. In addition, the present disclosure demonstrates the synthesis of novel electrophilic initiators wi
A chemoenzymatic asymmetric synthesis of the hydroxy acid segment of schulzeines B and C
Biswas, Sucheta,Chattopadhyay, Subrata,Sharma, Anubha
experimental part, p. 27 - 32 (2010/04/24)
A chemoenzymatic asymmetric synthesis of the title compound was developed by a building-block approach. The key steps of the synthesis were (i) an enantioselective lipase-catalyzed acylation of a secondary alcohol, (ii) an efficient diastereoselective add
Elucidation of the stereostructure of the annonaceous acetogenin (+)-montecristin through total synthesis
Harcken,Brueckner
, p. 40 - 54 (2007/10/03)
Total syntheses of ent-5-epi-montecristin (1a) and of (-)-montecristin (1b) were accomplished. The stereocenters of compounds 1a and 1b were established by asymmetric dihydroxylations of the trans-configurated β,γ-unsaturated esters 6 (→4, up to 80% ee; S
