(-)-14-O-acetyl indolactam V | 91403-61-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (-)-14-O-acetyl indolactam V
• 英文别名: (-)-14-O-acetylindolactam V；(-)-14-O-acetylindolactam-V；[(10S,13S)-9-methyl-11-oxo-10-propan-2-yl-3,9,12-triazatricyclo[6.6.1.04,15]pentadeca-1,4(15),5,7-tetraen-13-yl]methyl acetate
• CAS: 91403-61-1
• 化学式: C₁₉H₂₅N₃O₃
• 分子量: 343.426
• InChiKey: WJBVMJYASZWGBL-KSSFIOAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  74.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (-)-14-O-acetyl indolactam V 在 lithium aluminium tetrahydride 、 三氯化铝 、 ammonium acetate 、 三氯氧磷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.6h， 生成
  参考文献：
  名称：

  吲哚生物碱肿瘤启动子telocicins的光不稳定衍生物：合成，生物活性和光亲和标记研究。

  摘要：

  合成了新的对光不稳定的Teleocidin衍生物（Az-A-1，Az-C 7和Az-C 2），并通过与肿瘤促进活性相关的三种体外生物测定法进行了检查。Az-A-1（15）和Az-C 7的两个差向异构体（11a，11b）的活性比电离蛋白的基本结构（-）-吲哚-V-（1）高约10至100倍。通过使用可商购的3 H标记的琥珀酰亚胺基-4-叠氮基苯甲酸酯，可以合成具有超过40Ci / mmol的比活性的3 H标记的探针。[ 3 H] Az-A-1和[ 3 H] Az-C 7的特异性结合对于小鼠表皮微粒部分而言，远程信息素的靶组织在约20nM是可饱和的。使用[ 3 H] Az-A-1在颗粒级分上进行光亲和性标记，支持了最近的假设，即telociocidins 7位的烷基链与邻近受体位点的磷脂相互作用。SDS凝胶电泳的光标记颗粒级分表明存在两种蛋白质（约30和50kD），它们分别由[ 3 H] Az-A-1和[

  DOI：

  10.1016/s0040-4020(01)80236-2
• 作为产物：
  描述：

  吲哚内酰胺 V 、 乙酰氯 以 吡啶 为溶剂， 以95%的产率得到(-)-14-O-acetyl indolactam V
  参考文献：
  名称：

  Irie, Kazuhiro; Hagiwara, Nobuyuki; Koshimizu, Koichi, Agricultural and Biological Chemistry, 1985, vol. 49, # 5, p. 1441 - 1446

  摘要：

  DOI：

文献信息

• New probes for receptor analysis of tumor promoters synthesis of fluorescent derivatives of (-)-indolactam v,the basic ring-structure of teleocidins
  作者：Kazuhiro Irie、Nobuyuki Hagiwara、Koichi Koshimizu

  DOI：10.1016/s0040-4020(01)87701-2

  日期：——

  A biologically active fluorescent compound, (-)-7-(2-- dansylaminoethyl)indolactam V(), was synthesized from (-)-indolactam V () in 6 steps together with an inactive fluorescent derivative, (-)-7-(2--dansylaminoethyl)-14--methylindolactam V (). (-)-Indolactam V () exists as two stable conformers in solution at room temperature. The effect of substituents and substitution positions of the indole ring

  由（-）-吲哚内酰胺V（）分6步合成了具有生物活性的荧光化合物（-）-7-（2--丹酰氨基乙基）吲哚内酰胺V（）以及无活性的荧光衍生物（-）-7- （2--腺苷氨基乙基）-14--甲基吲哚内酰胺V（）。（-）-Indolactam V（）在室温下以两种稳定的构象形式存在于溶液中。详细讨论了吲哚环的取代基和取代位置对（-）-吲哚内酰胺V（）这两个构象态的影响。
• Synthesis of a biologically active fluorescent indolactam derivative; A method of preparing new probes for receptor analysis of tumor promoters
  作者：Kazuhiro Irie、Nobuyuki Hagiwara、Koichi Koshimizu

  DOI：10.1016/s0040-4039(00)95489-3

  日期：——

  A biologically active fluorescent compound, (−)-7-(2-N-dansylaminoethyl)indolactam V, was synthesized from (−)-indolactam V, which has the basic ring-structure of teleocidins. The effect of substituents on the two conformational states of (−)-indolactam V in solution was also discussed.

  由具有遥距菌素的基本环结构的（-）-吲哚内酰胺V合成生物活性荧光化合物（-）-7-（2-N-丹酰氨基乙基）吲哚内酰胺V。还讨论了取代基对溶液中（-）-吲哚酰胺V的两个构象态的影响。
• Structure and tumor-promoting activity of new teleocidin-related metabolites (blastmycetins) from Streptoverticillium blastmyceticum.
  作者：Nobuyuki HAGIWARA、Kazuhiro IRIE、Atsushi FUNAKI、Hideo HAYASHI、Motoo ARAI、Koichi KOSHIMIZU

  DOI：10.1271/bbb1961.52.641

  日期：——

  Six new teleocidin-related compounds (3-8) together with (-)-N13-desmethylindolactam V (9) were found in the culture broth of Streptoverticillium blastmyceticum NA34-17 producing tumor-promoting indole alkaloids. Compounds 3-8 proved to be a dimer of (-)-indolactam V(3), which bound through a methylene group at position 7, 2-oxy derivatives of (-)-indolactam V (4-7) and 14-O-methylteleocidin A-l (8), respectively. Their tumor-promoting activities are also discussed.X

  在产生促肿瘤吲哚生物碱的链轮丝菌 NA34-17 的培养液中发现了六种新的 teleocidin 相关化合物 (3-8) 以及 (-)-N13-desmethylindolactam V (9)。化合物3-8被证明是(-)-吲哚内酰胺V(3)的二聚体，其通过7位的亚甲基、(-)-吲哚内酰胺V(4-7)和14-O的2-氧基衍生物结合分别为-甲基teleocidin A-1 (8)。还讨论了它们的促肿瘤活性。X
• Synthesis, conformation and PKC isozyme surrogate binding of indolinelactam-Vs, new conformationally restricted analogues of (−)-indolactam-V
  作者：Yu Nakagawa、Kazuhiro Irie、Yusuke Komiya、Hajime Ohigashi、Ken-ichiro Tsuda

  DOI：10.1016/j.tet.2003.08.081

  日期：2004.8

  New conformationally restricted analogues of tumor promoter (-)-indolactam-V (1), indolinelactam-Vs (8, 11) and their hexyl derivatives at position 1 or 7 (9, 10, 12, 13), were synthesized from 1. (3R)-Indolinelactam-V (8) adopted a conformation similar to the twist form of 1 with a cis amide, while the conformation of (3S)-indolinelactam-V (11) was close to that of the sofa form of 1 with a trans amide. 7-Hexyl derivatives of 8 and 11 (10, 13) showed binding affinities for Cl domains of protein kinase C (PKC) isozymes compared to 1, but exhibited little selectivity among these PKC isozymes. However, introduction of the hexyl group at position 1 of 8 and 11 significantly enhanced their binding selectivity for novel PKC isozymes. The best selectivity for novel PKC isozymes was observed in (3S)-1-hexylindolinelactam-V (12) with a sofa-like conformation. These results suggest that a sofa-restricted analogue of 1 with a hydrophobic chain at an appropriate position would be a promising lead for designing agents with a high selectivity for novel PKC isozymes. (C) 2004 Elsevier Ltd. All rights reserved.
• Design and physicochemical properties of new fluorescent ligands of protein kinase C isozymes focused on CH/π interaction
  作者：Takuya Sugimoto、Koji Itagaki、Kazuhiro Irie

  DOI：10.1016/j.bmc.2007.10.045

  日期：2008.1

  Phorbol ester-type tumor promoters such as indolactarn-V (IL-V, 1) bind to the Cl domains of protein kinase C (PKC) isozymes. A more convenient method to investigate the interaction between each tumor promoter and PKC C1 domain is needed. Focusing on our recent finding that the indole ring of IL-V is involved in the CH/pi interaction with Pro-11 of the PKC delta-CIB domain, we developed new fluorescent probes (2-4) from IL-V by forming a pyrroloindazole ring. Compound 2 without a substituent at the pyrroloindazole ring bound most strongly to PKC C1 domains with a potency similar to IL-V, but its fluorescent intensity was the weakest of any of the probes, Although the binding affinity of 3 with a methyl group was significantly weaker than that of IL-V, 4 with a trifluoromethyl group showed moderate affinity and the most potent fluorescence intensity. The fluorescence intensity and emission maxima of 4 changed significantly when bound to the PKC delta-CIB peptide in both the presence and absence of phosphatidylserine. These results suggest that 4 could be a useful probe for analyzing the interaction of tumor promoters with PKC C1 domains. (c) 2007 Elsevier Ltd. All rights reserved.