tulearin A | 1005147-99-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: tulearin A
• 英文别名: [(3R,4R,6S,9S,10S,13E,16R,18S)-4,10-dihydroxy-3,6,16-trimethyl-18-[(1E,3E)-2-methylnona-1,3-dienyl]-2-oxo-1-oxacyclooctadec-13-en-9-yl] carbamate
• CAS: 1005147-99-8
• 化学式: C₃₁H₅₃NO₆
• 分子量: 535.765
• InChiKey: IKWWLIZHWPWWDY-HYKJIFQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  119
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tulearin A 在 氨 作用下， 以 甲醇 、 水 为溶剂， 以83%的产率得到
  参考文献：
  名称：

  Tulearins A, B, and C; structures and absolute configurations

  摘要：

  The relative configuration of tulearin A (1) is determined by X-ray diffraction analysis of a cyclic carbonate derivative 2 and the absolute configuration (2R,3R,5S,8S,9S,15R,17S) from the 9-MTPA-esters 1R and 1S is determined using the modified Mosher's method. A mechanism for the unexpected formation of carbonate 2 is suggested. Two N-phenyltriazolinedione derivatives 3 and 4 are also prepared. Two additional tulearins, B and C (5 and 6) are isolated in very small amounts and their structures are elucidated by spectroscopic means. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.04.028

文献信息

• Derivatives of Salarin A, Salarin C and Tulearin A—Fascaplysinopsis sp. Metabolites
  作者：Lee Zur、Ashgan Bishara、Maurice Aknin、Drorit Neumann、Nathalie Ben-Califa、Yoel Kashman

  DOI：10.3390/md11114487

  日期：——

  Derivatives of salarin A, salarin C and tulearin A, three new cytotoxic sponge derived nitrogenous macrolides, were prepared and bio-evaluated as inhibitors of K562 leukemia cells. Interesting preliminary SAR (structure activity relationship) information was obtained from the products. The most sensitive functionalities were the 16,17-vinyl epoxide in both salarins, the triacylamino group in salarin A and the oxazole in salarin C (less sensitive). Regioselectivity of reactions was also found for tulearin A.

  从海绵中提取的三种新的细胞毒性含氮大环内酯——salarin A、salarin C和tulearin A的衍生物，被制备并生物评价为K562白血病细胞的抑制剂。从这些产物中获得了有趣的初步的结构活性关系（SAR）信息。其中最敏感的功能基团包括salarin中16,17位的乙烯基环氧化物、salarin A中的三酰氨基团以及salarin C中的噁唑环（较不敏感）。tulearin A的反应还表现出区域选择性。
• Tulearins A, B, and C; structures and absolute configurations
  作者：Ashgan Bishara、Amira Rudi、Israel Goldberg、Maurice Aknin、Yoel Kashman

  DOI：10.1016/j.tetlet.2009.04.028

  日期：2009.7

  The relative configuration of tulearin A (1) is determined by X-ray diffraction analysis of a cyclic carbonate derivative 2 and the absolute configuration (2R,3R,5S,8S,9S,15R,17S) from the 9-MTPA-esters 1R and 1S is determined using the modified Mosher's method. A mechanism for the unexpected formation of carbonate 2 is suggested. Two N-phenyltriazolinedione derivatives 3 and 4 are also prepared. Two additional tulearins, B and C (5 and 6) are isolated in very small amounts and their structures are elucidated by spectroscopic means. (C) 2009 Elsevier Ltd. All rights reserved.