6-[(2E)-2-丁烯-2-基]-2,4,7-三氯-3-羟基-8-甲氧基-1,9-二甲基-11H-二苯并[b,e][1,4]二氧杂卓-11-酮 | 10089-10-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 中文名称: 6-[(2E)-2-丁烯-2-基]-2,4,7-三氯-3-羟基-8-甲氧基-1,9-二甲基-11H-二苯并[b,e][1,4]二氧杂卓-11-酮
• 中文别名: 巢曲菌素
• 英文名称: nidulin
• 英文别名: 1-[(E)-but-2-en-2-yl]-2,8,10-trichloro-9-hydroxy-3-methoxy-4,7-dimethylbenzo[b][1,4]benzodioxepin-6-one
• CAS: 10089-10-8
• 化学式: C₂₀H₁₇Cl₃O₅
• 分子量: 443.711
• InChiKey: FSINAZMQWFDQSD-VOTSOKGWSA-N

物化性质

• 熔点：
  180°
• 沸点：
  601.9±55.0 °C(Predicted)
• 密度：
  1.412±0.06 g/cm3(Predicted)
• 溶解度：
  DMF：可溶； DMSO：可溶；乙醇：可溶；甲醇：可溶

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-[(2E)-2-丁烯-2-基]-2,4,7-三氯-3-羟基-8-甲氧基-1,9-二甲基-11H-二苯并[b,e][1,4]二氧杂卓-11-酮 在 platinum(IV) oxide 氢气 作用下， 以 溶剂黄146 为溶剂， 以65 mg的产率得到dihydronidulin
  参考文献：
  名称：

  地泼酮的合成。第18部分。

  摘要：

  3,4,7-三氯-3-羟基-8-甲氧基-1,9-二甲基-6-s-丁基二苯并[ b，e ] [1,4]二氧己平-11-one（dihydronidulin）（2 ），是二苯甲酮-grisadienedione-keten-depsidone互变的真菌地二酮尼杜林（4）的衍生物。

  DOI：

  10.1039/p19810000874
• 作为产物：
  描述：

  6-(2-丁烯-2-基)-2,4,7-三氯-3,8-二羟基-1,9-二甲基-11H-二苯并[b,e][1,4]二氧杂卓-11-酮 、 碘甲烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 6-[(2E)-2-丁烯-2-基]-2,4,7-三氯-3-羟基-8-甲氧基-1,9-二甲基-11H-二苯并[b,e][1,4]二氧杂卓-11-酮
  参考文献：
  名称：

  尼杜林衍生物的半合成和抗菌活性。

  摘要：

  为了评估化学骨架作为抗菌剂的潜力，已经合成了真菌二甲泼酮的衍生物尼杜林。降冰片素的烷基化，酰化和芳基化反应以区域选择性方式进行，主要产生8-O-取代的衍生物。许多半合成衍生物显示出比尼杜林更强的抗菌活性，特别是8-O-芳基醚衍生物显示出对革兰氏阳性细菌（包括耐甲氧西林金黄色葡萄球菌）的显着活性。

  DOI：

  10.1038/s41429-018-0133-0

文献信息

• Diphenyl ethers and depsidones from the endophytic fungus Aspergillus unguis BCC54176
  作者：Karoon Sadorn、Siriporn Saepua、Nantiya Bunbamrung、Nattawut Boonyuen、Somjit Komwijit、Pranee Rachtawee、Pattama Pittayakhajonwut

  DOI：10.1016/j.tet.2021.132612

  日期：2022.1

  aspergillusethers G−J (1–4), and one new depsidone, emeguisin D (7), together with eighteen known compounds have been isolated and characterized from the endophytic fungus Aspergillus unguis BCC54176. The chemical structures were established based on spectroscopic evidence in conjunction with a chemical transformation. Furthermore, the chemical structure of compound 7 was verified by single-crystal

  从内生真菌Aspergillus unguis BCC54176 中分离出四种新的二苯醚，曲霉醚 G-J ( 1 – 4 ) 和一种新的 depsidone，emmeguisin D ( 7 )，以及 18 种已知化合物。化学结构是基于光谱证据结合化学转化建立的。此外，化合物7的化学结构通过单晶X射线衍射数据得到验证。评估分离的化合物的生物活性。化合物7、 emeguisin C ( 10 ) 和 nidulin ( 14 ) 对蜡状芽孢杆菌具有抗菌活性MIC 值为 1.56 μg/mL，而 emeguisin A ( 8 )、nornidulin ( 13 )、2-chlorounguinol ( 16 ) 和 aspergillusidone C ( 21 ) 对刺炭疽菌具有相同的 MIC 值3.13 微克/毫升。化合物7对金黄色葡萄球菌也有活性，MIC 值为 1.56 μg/mL。然
• MYCOBACTERIUM MEMBRANE PROTEASE AS A TARGET FOR INHIBITORS OF INTRABACTERIAL pH HOMEOSTASIS
  申请人：Nathan Carl

  公开号：US20110190234A1

  公开（公告）日：2011-08-04

  The present invention is directed to methods and compounds for inhibiting bacterial growth and treating a bacterial infection in a subject. These methods involve providing an inhibitor of intrabacterial pH homeostasis, including inhibitors of the Mycobacterium tuberculosis Rv3671c gene encoded membrane protease. Methods for identifying novel compounds that disrupt intrabacterial pH homeostasis and their use for inhibiting bacterial growth and treating a bacterial infection in a subject are also disclosed.
• ANTIBIOTIC COMPOUNDS THAT INHIBIT BACTERIAL PROTEIN SYNTHESIS
  申请人：The Board of Regents of the University of Texas System

  公开号：US20160220510A1

  公开（公告）日：2016-08-04

  An aminoacylation/translation (AIT) system based on the protein synthesis system from the pathogen Pseudomonas aeruginosa , was used to screen chemical compounds for identifying inhibitors of protein synthesis. This system includes elongation factors: EF-Tu, EF-Ts and EF-G, aminoacyl tRNA synthetase (aaRS) specific for phenylalanine, PheRS, and ribosomes isolated from cultures of Pseudomonas aeruginosa . Compounds identified using this assay have been shown to contain broad spectrum activity against both Gram+ and Gram− pathogens. Methods of using the identified compounds, as well as derivatives and analogues of these compounds, as antimicrobial agents against bacterial infections are described.
• US8951992B2
  申请人：——

  公开号：US8951992B2

  公开（公告）日：2015-02-10
• [EN] NOVEL PEPTIDE ISOLATED FROM ASPERGILLUS NIDULANS AND PHARMACEUTICAL COMPOSITION CONTAINING THE SAME<br/>[FR] NOUVEAU PEPTIDE ISOLE A PARTIR D'ASPERGILLUS NIDULANS ET COMPOSITION PHARMACEUTIQUE LE RENFERMANT
  申请人：CHOSUN UNIVERSITY

  公开号：WO2006080625A1

  公开（公告）日：2006-08-03

  [EN] This invention relates to a novel peptide of Nidulin having antibiotic and antifungal activities, which is identified and isolated from Aspergillus nidulans , and relates to a pharmaceutical composition comprising the peptide as an effective component. Since the novel peptide of Nidulin has potent antibiotic and antifungal activities and has no toxicity, it can be used as preparations of a pesticide, which is non-toxic to human body, a food preservative, a cosmetics preservative, or preparations of a drug preservative.
  [FR] L'invention concerne un nouveau peptide de niduline qui possède des activités antibiotiques et antifongiques et qui est identifié et isolé à partir d'Aspergillus nidulans