139258-86-9Relevant academic research and scientific papers
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
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.
Motualevic acids and analogs: Synthesis and antimicrobial structure-activity relationships
Cheruku, Pradeep,Keffer, Jessica L.,Dogo-Isonagie, Cajetan,Bewley, Carole A.
scheme or table, p. 4108 - 4111 (2010/08/20)
Synthesis of the marine natural products motualevic acids A, E, and analogs in which modifications have been made to the ω-brominated lipid (E)-14,14-dibromotetra-deca-2,13-dienoic acid or amino acid unit are reported, together with antimicrobial activities against Staphylococcus aureus, methicillin-resistant S. aureus, Enterococcus faecium, and vancomycin-resistant Enterococcus.
Development of a concise and diversity-oriented approach for the synthesis of plecomacrolides via the diene-ene RCM
Lu, Kui,Huang, Mengwei,Xiang, Zheng,Liu, Yongxiang,Chen, Jiahua,Yang, Zhen
, p. 1193 - 1196 (2007/10/03)
A concise synthesis of the core structures of plecomacrolide with ring sizes varying from 16 to 19 atoms was achieved for the first time by the diene-ene ring-closing olefin metathesis reaction. This approach should allow access to the structurally divers
Method of treating dry eye disorders using 13(S)-HODE and its analogs
-
Page/Page column 3; 4, (2010/11/08)
The topical use of 13(S)-HODE and analogs are disclosed for the treatment of dry eye disorders.
Total synthesis of cytotoxic sponge alkaloids hachijodines F and G
Goundry, William R. F.,Baldwin, Jack E.,Lee, Victor
, p. 1719 - 1729 (2007/10/03)
The total synthesis of two cytotoxic sponge alkaloids hachijodines F and G has been achieved. The synthesis of both compounds utilises a common intermediate alkyne. By comparison of spectra the structure of the natural product has been confirmed.
Total synthesis of cytotoxic sponge alkaloids hachijodines F and G
Goundry, William R.F.,Lee, Victor,Baldwin, Jack E.
, p. 2745 - 2747 (2007/10/03)
The total synthesis of two cytotoxic sponge alkaloids hachijodines F (1) and G (2) via a common intermediate 3 is described.
Synthesis and reactivity of ω-aldehydophosphoranes; application to the preparation of α,β-unsaturated lactones.
Floc'h, Y. Le,Yvergnaux, F.,Toupet, L.,Gree, R.
, p. 742 - 759 (2007/10/02)
α,β-Unsaturated lactones 1 (n = 1 to 7) and symmetrical unsaturated macrodiolides 2 are obtained by a Wittig reaction using ω-aldehydophosphoranes under high dilution conditions.The corresponding phosphonium salts are prepared in 3 steps from commercially available ω-diols.This methodology is applied to the synthesis of an unsaturated macrolide, a precursor of Patulolid A and Patulolid C. Key words: intramolecular Wittig reaction / ω-aldehydophosphoranes / unsaturated lactones / unsaturated dilactones
