N-[2-(8,11,12,13-四氢-12-氧代吡啶并[4,3,2-mn][1,4]噻嗪并[3,2-b]吖啶-9-基)乙基]-乙酰胺 | 122271-41-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: N-[2-(8,11,12,13-四氢-12-氧代吡啶并[4,3,2-mn][1,4]噻嗪并[3,2-b]吖啶-9-基)乙基]-乙酰胺
• 英文名称: debromoshermilamine A
• 英文别名: shermilamine B；N-[2-(16-oxo-18-thia-2,12,15-triazapentacyclo[11.7.1.03,8.09,21.014,19]henicosa-1(20),3,5,7,9(21),10,12,14(19)-octaen-20-yl)ethyl]acetamide
• CAS: 122271-41-4
• 化学式: C₂₁H₁₈N₄O₂S
• 分子量: 390.466
• InChiKey: IHFPKDUIXNIBMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[2-(8,11,12,13-四氢-12-氧代吡啶并[4,3,2-mn][1,4]噻嗪并[3,2-b]吖啶-9-基)乙基]-乙酰胺 在 盐酸 、 水 作用下， 反应 5.0h， 生成 N-deacetylshermilamine B
  参考文献：
  名称：

  Structures and Antimicrobial Activities of Pyridoacridine Alkaloids Isolated from Different Chromotypes of the Ascidian Cystodytes dellechiajei

  摘要：

  Three new pentacyclic alkaloids were isolated from different chromotypes of the western Mediterranean ascidian Cystodytes dellechiajei. The purple color morph collected in Catalonia contained the known compounds kuanoniamine D (1), shermilamine B (2), N-deacetylkuanoniamine (3), and styelsamine C (4) and a new alkaloid named N-deacetylshermilamine B (5). The green color morph collected in the Balearic Islands contained the known compounds 11-hydroxyascididemin (6) and 8,9-dihydro-11-hydroxyascididemin (7) and two new alkaloids named cystodimine A (8) and cystodimine B (9). The blue color morph collected in Catalonia yielded the known compound ascididemin (10). The structures of all compounds were elucidated on the basis of spectroscopic data, mainly 1D and 2D NMR data. The antimicrobial potential of the pyridoacridine alkaloids isolated from each color morph was evaluated and compared.

  DOI：

  10.1021/np900751k
• 作为产物：
  描述：

  N-[2-[7-(2-azidophenyl)-2-oxo-5,6-dihydro-1H-pyrido[2,3-f][1,4]benzothiazin-5-yl]ethyl]acetamide 在 苯乙酮 作用下， 以 氯苯 为溶剂， 反应 3.0h， 以67%的产率得到N-[2-(8,11,12,13-四氢-12-氧代吡啶并[4,3,2-mn][1,4]噻嗪并[3,2-b]吖啶-9-基)乙基]-乙酰胺
  参考文献：
  名称：

  A Unified Strategy for the Synthesis of Sulfur-Containing Pyridoacridine Alkaloids: Antitumor Agents of Marine Origin

  摘要：

  Details of the total synthesis of the major classes of sulfur-containing pyridoacridine alkaloids, dercitins, kuanoniamines, diplamine, and shermilamine B, are described.

  DOI：

  10.1021/ja00155a010

文献信息

• Total Synthesis of Cystodytin J, Diplamine and Shermilamine B
  作者：M Ciufolini

  DOI：10.1016/00404-0399(50)08487-

  日期：1995.7.3
• US5278168A
  申请人：——

  公开号：US5278168A

  公开（公告）日：1994-01-11
• US5432172A
  申请人：——

  公开号：US5432172A

  公开（公告）日：1995-07-11
• [EN] BIOLOGICAL APPLICATIONS OF ALKALOIDS DERIVED FROM THE TUNICATE EUDISTOMA sp.<br/>[FR] APPLICATIONS BIOLOGIQUES D'ALCALOIDES DERIVES DU TUNICIER EUDISTOMA sp.
  申请人：THE RESEARCH FOUNDATION OF STATE UNIVERSITY OF NEW YORK

  公开号：WO1994003433A1

  公开（公告）日：1994-02-17

  (EN) Biological applications of synthetic and natural alkaloids derived from the tunicate $i(Eudistoma sp.), as well as the preparation of synthetic pyridoacridines, and particularly methods for the synthesis of Eilatin are disclosed. A method regulating cell growth includes contacting one or more cells with an effective concentration of compound for regulating cell growth. These compounds include: Segoline A, Segoline B, Isosegoline A, Norosegoline, Debromoshermilamine, Eilatin, 4-methylpyrido[2,3,4-kl] acridine, pyrido[2,3,4-kl]acridine, 1-acetyl-2, 6-dimethylpyrido[2,3,4-kl]acridine, and derivatives and combinations of these compounds.(FR) L'invention se rapporte aux applications biologiques d'alcaloïdes synthétiques et naturels dérivés du tunicier $i(Eudistoma sp.), ainsi qu'à la préparation de pyridoacridines synthétiques, et plus particulièrement à des procédés de synthèse de l'Eilatine. Un procédé de régulation de la prolifération cellulaire consiste à mettre une ou plusieurs cellules en contact avec une concentration efficace d'un composé destiné à réguler la prolifération cellulaire. Ces composés sont les suivants: Ségoline A, Ségoline B, Isoségoline A, Noroségoline, Debcomoshermilamine, Eilatine, 4-méthylpyrido[2,3,4-kl]acridine, pyrido[2,3,4-kl]acridine, 1-acétyl-2, 6-diméthylpyrido[2,3,4-kl]acridine, des dérivés et des combinaisons de ces composés.
• A Unified Strategy for the Synthesis of Sulfur-Containing Pyridoacridine Alkaloids: Antitumor Agents of Marine Origin
  作者：Marco A. Ciufolini、Yong-Chun Shen、Michael J. Bishop

  DOI：10.1021/ja00155a010

  日期：1995.12

  Details of the total synthesis of the major classes of sulfur-containing pyridoacridine alkaloids, dercitins, kuanoniamines, diplamine, and shermilamine B, are described.