CAS: 96829-59-3; (S)-(S,4Z,7Z)-1-((2S,3S)-3-Hexyl-4-Oxooxetan-2-yl)Trideca-4,7-Dien-2-Yl 2-Formamido-4-Methylpentanoate

该化合物是胰腺脂酶的强效抑制剂,是消化饮食脂肪的关键酶,被归类为脂酶抑制剂,主要用于肥胖症的管理.利普塔廷的化学结构具有复杂的内酯环和独特的脂肪酸侧链,有助于其生物活动.作为药剂,它通过防止肠胃吸收饮食脂肪,从而减少热量摄入量而发挥作用.利普塔廷通常口服,并经常与降低热量的饮食和运动一起用于有效的体重管理.其行动机制涉及与活跃的胰腺脂酶点形成共振联系,从而抑制其活动.虽然利普塔廷有效,但利普塔廷可以对消化系统中的未食脂肪造成胃肠侧效应.

结构式图片

上下游产品

CAS号5338-45-4 2-formamido-4-m... | CAS号108102-73-4 (3S,4S,2'R)-3-H... | CAS号10340-23-5 顺-3-壬烯-1-醇 | CAS号31823-43-5 (Z)-3-nonen-1-al | CAS号136695-81-3 (3Z)-1-bromo-3-... | CAS号120018-49-7 (Z)-3-nonenal d... | CAS号85924-42-1 [(3Z)-3-nonen-1... | CAS号66-25-1 正己醛 | CAS号151509-75-0 Methyl (R)-(Z,Z...

合成工艺路线路线简述

  • 合成目标产物 Lipstatin 主要起始原料 Hexanal
  • (文献来源)合成步骤主要原料 Hexanal
📜顺-3-壬烯-1-醇置于吡啶,氢氟酸,四丁基氟化铵,Sodium Hexamethyldisilazane,二氯乙基铝,二异丁基氢化铝,三苯基膦,偶氮二甲酸二乙酯,二溴三苯基膦体系中,用 四氢呋喃,乙醚,正己烷,二氯甲烷,乙腈 作为反应溶剂,化学反应 78.25H,反应生成 奥利司他中间体
参考文献:An Approach To The Synthesis Of (-)-Lipstatin By Wittig Reaction And Lewis Acid-Promoted [2 + 2] Cycloaddition
标题:An Approach To The Synthesis Of (-)-Lipstatin By Wittig Reaction And Lewis Acid-Promoted [2 + 2] Cycloaddition
摘要:The Beta-Lactone Moiety Of (-)-Lipstatin 1,A Potent Inhibitor Of Pancreatic Lipase,Is Prepared Via A Lewis Acid-Promoted [2 + 2] Cycloaddition Between Hexyltrimethylsilyl Ketene 3 And The (Z,Z)-Dienic Aldehyde 4,Obtained From Hexanal By Two Stereoselective Wittig Reactions.
DOI:10.1039/p19930001549

海关参考信息

专利信息


专利号:US-8124794-B2
优先权日:2002-04-17
标题:Method for the asymmetric synthesis of beta-lactone compounds
发明人:SMITH JEFFREY W; AXELROD FUMIKO; KRIDEL STEVEN J; ROMO DANIEL; PUROHIT VIKRAM; MA GIL
权利人:SMITH JEFFREY W; AXELROD FUMIKO; KRIDEL STEVEN J; ROMO DANIEL; PUROHIT VIKRAM; MA GIL; SANFORD BURNHAM MED RES INST
摘要:The present invention features methods of treating a cancer in a subject by administering an effective amount of a beta-lactone to the subject. The invention also features methods of inhibiting angiogenesis in a subject by administering an effective amount of an inhibitor of fatty acid synthase to the subject. These methods can be used to treat a variety of cancers and other diseases and conditions. The invention also features methods of identifying beta-lactones and other compounds that can be used in the methods of the invention for the treatment of tumors, inhibition of angiogenesis, and the treatment of diseases and conditions that involve pathological angiogenesis. The invention also features methods of synthesizing beta-lactones and features novel beta-lactone compounds.

专利号:WO-2016037566-A1
优先权日:2014-09-09
标 题:Use of antroqiononol for treating obesity, and process for preparation of antroquinonol
发明人:WENG CHING-FENG; CHEN CHIN-PIAO; SHIVAJI SULAKE ROHIDAS; Huang zi-ling
权利人:WENG CHING-FENG
摘要:Provided is the use of antroquinonol for manufacturing a composition or medicament for treating obesity. In addition, new processes for the total synthesis of antroquinonol and new compounds produced during the processes are disclosed.

专利号:US-10655153-B2
优先权日:2017-03-14
标 题 :Chemoenzymatic synthesis of peptide beta-lactones and beta-hydroxy acids
发明人:WENCEWICZ TIMOTHY A; SCHAFFER JASON E; RECK MARGARET R
权利人:WENCEWICZ TIMOTHY A; SCHAFFER JASON E; RECK MARGARET R; UNIV WASHINGTON
摘要:Methods of producing peptide beta-lactones and beta-hydroxy acids are disclosed that include contacting a beta-hydroxy-alpha-amino acid, an aryl carrier protein (ObiD), and ATP with a non-ribosomal protein synthetase. A continuous flow reactor is disclosed that includes an elongate conduit with at least one region that includes a first region with a non-ribosomal protein synthetase immobilized to a substrate. The non-ribosomal protein synthetase of the continuous flow reactor is configured to contact a flow of a reaction mixture that includes a beta-hydroxy-alpha-amino acid and an aryl carrier protein. The non-ribosomal protein synthetase is further configured to release a peptide beta-lactone into the flow of the reaction mixture.

专利号:US-8598153-B2
优先权日:2006-09-22
标题 :Method of treatment using fatty acid synthesis inhibitors
发明人:SINGH SHEO B; TOTA MICHAEL R; WANG JUN
权利人:SINGH SHEO B; TOTA MICHAEL R; WANG JUN; MERCK SHARP & DOHME
摘要:The present invention relates to natural products that possess fatty acid synthesis inhibitor activity and can be used to treat and prevent diseases such as obesity, cancer, diabetes, fungal infections, Mycobacterium tuberculosis infections, malarial infections and other apicomplexan protozoal diseases.

专利号:US-5902886-A
优先权日:1997-01-23
标题 :Method for synthesizing oxetan-2-ones and intermediates for their preparation
发明人:SCHICK HANS; WEDLER CHRISTINE
摘要:A method is described for the synthesis of oxetan-2-ones comprising protection of the hydroxy group of an hydroxy ester with an acid-labile acetal protecting group, reduction of this O-protected hydroxy ester to an O-protected hydroxy aldehyde, condensation of this aldehyde with a metal enolate of an activated carboxylic acid derivative and spontaneous deprotection of the hydroxy group during the acidic workup procedure. Using the new O-protected hydroxy aldehydes as intermediates the oxetan-2-ones can be obtained after separation in diastereomerically and enantiomerically pure form, in a remarkably reduced number of steps, and in a significantly improved overall yield.

专利号:US-7495108-B2
优先权日:2004-02-19
标 题:Imidazoline derivatives having CB1-antagonistic activity
发明人:LANGE JOSEPHUS H M; KRUSE CORNELIS G; VAN STUIVENBERG HERMAN H
权利人:SOLVAY PHARM BV
摘要:The present invention relates to 1,2,4-tri-substituted imidazoline derivatives, to methods for the preparation of these compounds, to novel intermediates useful for the synthesis of said imidazoline derivatives, to methods for the preparation of these intermediates, to pharmaceutical compositions containing one or more of these imidazoline derivatives as active ingredient, as well as to the use of these pharmaceutical compositions for the treatment of psychiatric and neurological disorders. The compounds have the general formula (I) n nwherein the symbols have the meanings given in the specification.

供应商参考报价(招募中)

品牌试剂参考报价(招募中)

📌 第三方产品分析报告

✅ COA系统入驻 | 共享模式

主要参考文献


1: Zhu T, Wang L, Wang W, Hu Z, Yu M, Wang K, Cui Z. Enhanced production of lipstatin from Streptomyces toxytricini by optimizing fermentation conditions and medium. J Gen Appl Microbiol. 2014;60(3):106-11. doi: 10.1128/AEM.01765-14. Epub 2014 Sep 19.
3: Kumar P, Dubey KK. Modulation of fatty acid metabolism and tricarboxylic acid cycle to enhance the lipstatin production through medium engineering in Streptomyces toxytricini. Bioresour Technol. 2016 Aug;213:64-68. doi: 10.1016/j.biortech.2016.01.133. Epub 2016 Feb 11. doi: 10.1007/s00253-010-2587-2. Epub 2010 May 2.
5: Schuhr CA, Eisenreich W, Goese M, Stohler P, Weber W, Kupfer E, Bacher A. Biosynthetic precursors of the lipase inhibitor lipstatin. J Org Chem. 2002 Apr 5;67(7):2257-62. doi: 10.1039/c0cc01276a. Epub 2010 Jun 24. Epub 2016 Jun 26. Epub 2014 Jan 14. doi: 10.1007/s12275-011-1122-1. Epub 2011 Jun 30. doi: 10.1007/s00284-017-1420-x. Epub 2017 Dec 18. doi: 10.1007/s13205-017-1049-2. Epub 2017 Dec 26.

合成参考文献


摘要:Kleemann, A.; Engel, J.; Kutscher, B.; Reichert, D., Pharmaceutical Substances[Online], Thieme: Stuttgart, (2008).
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