CAS: 67-99-2; Gliotoxin

该化合物是一种由某些真菌,特别是象素Aspergillus和Peniclium所生产的第二代代代谢物,被归类为含有硫化物的化合物,以其强效免疫抑制性特性而著称.Gliotoxin展示了一个以双环核为特征的复杂结构,其中包括一个硫化环和乳腺.该化合物因其抑制各种细胞过程的能力而进行了研究,包括吸附和免疫细胞的激活,使其对医学研究和毒理学都感兴趣.Gliotoxin因其在真菌病发发中的潜在作用而得到承认,因为它能够对某些真菌感染的剧变产生产生作用.就物理特性而言,Gliotoxin通常没有色,不会腐烂的黄色固体,有机溶剂中溶解,并且分子重量相对较低.由于它的生物活动,Gliotoxin是正在进行的研究的课题,特别是因为它对人类健康及其潜在的治疗应用产生影响.

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上下游产品

CAS号1402592-69-1 (3aS,5S,6aR,7S,... | CAS号1402592-87-3 (2S,7S,7aS)-1-t... | CAS号19079-11-9 Pyrazino[1,2-a]... | CAS号74149-38-5 二(甲硫基)焦霉毒素

合成工艺路线路线简述

  • 合成目标产物 Gliotoxin 主要起始原料 Ethanamine, N-[(3,5-Dichlorophenyl)Methylene]-2,2-Diethoxy-
  • (文献来源)合成步骤主要原料 Ethanamine, N-[(3,5-Dichlorophenyl)Methylene]-2,2-Diethoxy-
7C-Hydroxy-4-Hydroxymethyl-2ξ-(4-Methoxy-Phenyl)-13-Methyl-(6Ac)-7,11-Dihydro-6Ah-4R,11Ac-Azaethano-[1,3,5]Dithiazepino[5,4-A]Indole-5,12-Dione置于高氯酸,二甲基硫,间氯过氧苯甲酸体系中,化学反应生成 胶霉素
参考文献:胶体毒素,脱氢胶体毒素和透明质酸的全合成
标题:胶体毒素,脱氢胶体毒素和透明质酸的全合成
摘要:描述了用于合成上皮哌嗪二酮的两种通用方法,方案19中的方法a和方法b.外消旋和旋光性神经毒素(1)和外消旋脱氢神经毒素(53)的总合成通过方法a进行,而外消旋透明石蛋白(52)的全合成.
DOI:10.1016/s0040-4020(01)97960-8

海关参考信息

专利信息


专利号:US-7723082-B2
优先权日:2002-06-21
标题 :Polynucleotides and polypeptides coded by said polynucleotides involved in the synthesis of diketopiperazine derivatives
发明人:GONDRY MURIEL; GENET ROGER; LAUTRU SYLVIE; PERNODET JEAN-LUC
权利人:COMMISSARIAT ENERGIE ATOMIQUE; CENTRE NAT RECH SCIENT
摘要:The invention concerns novel isolated natural or synthetic polynucleotides and polypeptides coded by said polynucleotides, involved in the synthesis of diketopiperazine derivatives, vectors comprising said polynucleotides, micro-organisms transformed with said polynucleotides, uses of said polynucleotides and said polypeptides, as well as methods for the synthesis of diketopiperazine derivatives, including cyclodipeptides and diketopiperazine derivatives 3- and 6-substituted by α,β-unsaturated amino acid side chains.

专利号:US-5817751-A
优先权日:1994-06-23
标 题 :Method for synthesis of diketopiperazine and diketomorpholine derivatives
发明人:SZARDENINGS ANNA KATRIN; CAMPBELL DAVID
权利人:AFFYMAX TECH NV
摘要:The present invention relates to the areas of organic and medicinal chemistry. More specifically, the present invention is concerned with combinatorial and solid phase methods for the synthesis of diverse diketopiperazine derivatives, and the use of such methods to create libraries of diverse diketopiperazine derivatives. The present invention has application in the areas of chemical synthesis, the screening for new diketopiperazine derivatives having beneficial medical properties and the use of such screening to provide compositions and methods including diketopiperazine derivatives for treating disease.

专利号:US-2005080260-A1
优先权日:2003-04-22
标 题 :Preparation of prodrugs for selective drug delivery
发明人:MILLS RANDELL L; WU GUO-ZHANG
摘要:Synthesis of a chemical compound having the formula A-B-C that may serve for applications such as drug delivery where A is a chemiluminescent, moiety, B is a photochromic moiety, and C is a biologically active moiety where A-B-C may serve as a prodrug. Novel synthetic methods of the present invention to form the prodrug comprised the steps of (1) forming a benzophenone, (2) forming a diaryl ethylene, (3) attaching a phthalimide moiety to at least one of the aryl groups of the ethylene to form a phthalimide-ethylene conjugate, (4) condensing two ethylene-phthalimide conjugates to form a phthalimide-pentadiene conjugate, (5) converting the phthalimide to the phthalhydrazide by reaction with hydrazine to form a carrier compound according to the present invention, and (6) reacting the carrier compound with an nucleophilic moiety of the drug to form the corresponding prodrug. Alternatively the carrier can be prepared by using the halo-substituted diaryl ethylene to make the corresponding cationic leuco dye-like compound with known methods. The cationic compound then is protected by reacting with a nucleophile and coupled with the aminophathalimide by palladium-catalyzed amination to form the protected phthalimide-pentadiene conjugate. The latter is refluxed with hydrazine to convert its phthalimide to the phthalhydrazide and acidified to give the carrier. An additional aspect of the present invention relates to the use of these compounds as antiviral agents for the treatment of viral infections such as HIV and as anticancer agents for the treatment of cancers such as bowel, lung, and breast cancer.

专利号:WO-9600391-A1
优先权日:1994-06-23
标题:Methods for the synthesis of diketopiperazines
发明人:CAMPBELL DAVID; GALLOP MARK A; GORDON ERIC M; LOOK GARY C; PATEL DINESH; SZARDENINGS ANNA KATRIN
权利人:AFFYMAX TECH NV; CAMPBELL DAVID; GALLOP MARK A; GORDON ERIC M; LOOK GARY C; PATEL DINESH; SZARDENINGS ANNA KATRIN
摘要:Libraries of diverse diketopiperazines bound to a support and methods for synthesizing diketopiperazines on a solid support are described. These libraries have utility in the area of drug design as they can be screened against biological substances to identify compounds which have desirable biological activity.

专利号:US-2009011476-A1
优先权日:2005-08-19
标 题 :Gene cluster and method for the biosynthesis of terrequinone a
发明人:HOFFMEISTER DIRK; KELLER NANCY P
权利人:WISCONSIN ALUMNI RES FOUND
摘要:The present invention provides a novel gene cluster containing five genes (tdiA-E) involved in indole alkaloid synthesis. Disruption of tdiB, encoding an enzyme with prenyltransferase activity, transferring dimethylallylpyrophosphate to C-2 of an indole structure, eliminated the production of the antitumor compound terrequinone A, a metabolite not known from A. nidulans . The invention further provides a method for expressing terrequinone A in a host cell and isolating purified terrequinone A therefrom.

专利号:US-2006051837-A1
优先权日:2002-06-21
标 题 :Polynucleotides and polypeptides coded by said polynucleotides involved in the synthesis of diketopiperazine derivatives
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主要参考文献


1: Owens RA, O'Keeffe G, Smith EB, Dolan SK, Hammel S, Sheridan KJ, Fitzpatrick DA, Keane TM, Jones GW, Doyle S. Interplay between Gliotoxin Resistance, Secretion, and the Methyl/Methionine Cycle in Aspergillus fumigatus. Eukaryot Cell. 2015 Sep;14(9):941-57. doi: 10.1128/EC.00055-15. Epub 2015 Jul 6.
2: Dolan SK, O'Keeffe G, Jones GW, Doyle S. Resistance is not futile: gliotoxin biosynthesis, functionality and utility. Trends Microbiol. 2015 Jul;23(7):419-28. doi: 10.1016/j.tim.2015.02.005. Epub 2015 Mar 10. Review. doi: 10.1099/mic.0.079210-0. Epub 2014 Jul 31. doi: 10.1016/j.chembiol.2014.07.006. doi: 10.1186/1471-2164-15-894.
6: Jia X, Chen F, Pan W, Yu R, Tian S, Han G, Fang H, Wang S, Zhao J, Li X, Zheng D, Tao S, Liao W, Han X, Han L. Gliotoxin promotes Aspergillus fumigatus internalization into type II human pneumocyte A549 cells by inducing host phospholipase D activation. Microbes Infect. 2014 Jun;16(6):491-501. doi: 10.1016/j.micinf.2014.03.001. Epub 2014 Mar 14. doi: 10.1371/journal.pone.0093685. eCollection 2014.

合成参考文献


参考文献:10.18632/aging.100005
摘要:Singh SP, Niemczyk M, Zimniak L, Zimniak P. Fat accumulation in Caenorhabditis elegans triggered by the electrophilic lipid peroxidation product 4-hydroxynonenal (4-HNE). Aging (Albany NY). 2008 Dec 18;1(1):68–80.
参考文献:10.4103/2152-7806.81969
摘要:Kasper EM, Bartek J, Johnson S, Kasper BS, Pavlakis M, Wong M. Post-transplant aspergillosis and the role of combined neurosurgical and antifungal therapies under belatacept immunosuppression. Surg Neurol Int. 2011;2():75.
参考文献:10.1021/ja201311d
摘要:Scharf DH, Remme N, Habel A, Chankhamjon P, Scherlach K, Heinekamp T, Hortschansky P, Brakhage AA, Hertweck C. A dedicated glutathione S-transferase mediates carbon-sulfur bond formation in gliotoxin biosynthesis. J Am Chem Soc. 2011 Aug 17;133(32):12322–5. doi: 10.1021/ja201311d.
参考文献:10.1021/np2001573
摘要:Xu D, Ondeyka J, Harris GH, Zink D, Kahn JN, Wang H, Bills G, Platas G, Wang W, Szewczak AA, Liberator P, Roemer T, Singh SB. Isolation, Structure, and Biological Activities of Fellutamides C and D from an Undescribed Metulocladosporiella (Chaetothyriales) Using the Genome-Wide Candida albicans Fitness Test. J. Nat. Prod. 2011 Jul 13;74(8):1721–30. doi: 10.1021/np2001573.
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