(S,S)-9-decynylbenzolactam-V8 | 178247-23-9

• 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: (S,S)-9-decynylbenzolactam-V8
• 英文别名: (2S,5S)-9-dec-1-ynyl-5-(hydroxymethyl)-1-methyl-2-propan-2-yl-2,4,5,6-tetrahydro-1,4-benzodiazocin-3-one
• CAS: 178247-23-9
• 化学式: C₂₅H₃₈N₂O₂
• 分子量: 398.589
• InChiKey: ZFJCSDICMJVNSA-UPVQGACJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  52.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S,S)-9-decynylbenzolactam-V8 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 生成 (-)-Benzolactam-V8-310
  参考文献：
  名称：

  Role of the Hydrophobic Moiety of Tumor Promoters. Synthesis and Activity of 9-Alkylated Benzolactams.

  摘要：

  (-)-苯内酰胺-V8-310再现了远志素的活性构象和生物活性。在 BL-V8 的芳香核上合成了不同大小和形状的烷基，并以光学纯形式存在。结构-活性结果表明，C-9 位的疏水取代基对生物活性的出现起着关键作用。

  DOI：

  10.1248/cpb.44.1138
• 作为产物：
  描述：

  L-酪氨酸 在 bis-triphenylphosphine-palladium(II) chloride 、 palladium on activated charcoal 、 copper(l) iodide 咪唑 、 2,6-二甲基吡啶 、 盐酸 、 氢氧化钾 、 sodium hydroxide 、 sodium nitrate 、 sodium tetrahydroborate 、 锂硼氢 、 氯化亚砜 、 copper diacetate 、 lanthanum nitrate 、 二苯基磷酸 、 氢气 、 四丁基碘化铵 、 sodium cyanoborohydride 、 碳酸氢钠 、 potassium carbonate 、 对甲苯磺酸 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 、 氯仿 、 水 、 乙酸乙酯 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， -78.0~70.0 ℃ 、3.04 MPa 条件下， 反应 197.17h， 生成 (S,S)-9-decynylbenzolactam-V8
  参考文献：
  名称：

  General and Stereospecific Route to 9-Substituted, 8,9-Disubstituted, and 9,10-Disubstituted Analogues of Benzolactam-V8

  摘要：

  Nitration of the L-tyrosine derivative 9 provides the S-nitro compound 13', which is converted into amide 15 by reduction and protection. Nitration of 15 either ortho or para to the acetamido group gives 16 and 17. After reduction of the nitro group, the anilines 21b and 29b are coupled with triflate 22a, and then cyclized to afford lactams 24 and 31, respectively. By means of a Pd-catalyzed coupling reaction, 8-acetamido-4-decynylbenzolactam-V8 (26) and 9-decyny-10-acctamidobenzolactam-V8 (33) are obtained. The regioisomers 16 and 17 are transformed into a single isomer, 34, which is converted into 9-decynylbenzolactam-V8 (4). The K-i values for 4, 26, and 33 to displace PDBU binding from recombinant PKC alpha (PKC = protein kinase C) art! about 6, 173, and 16 nM. These results demonstrate that while the introduction of a substituent at; either the 8- or 10-position of the 9-substituted benzolactam-V8s lowers their binding affinity, these newly generated analogues still retain reasonably good potency for PKC.

  DOI：

  10.1021/jo990605h

文献信息

• Stereospecific synthesis of 9-substituted benzolactam-V8 from L-tyrosine via regioselective aromatic nitration
  作者：Dawei Ma、Wenjun Tang

  DOI：10.1016/s0040-4039(98)01598-6

  日期：1998.10

  A new protocol for the synthesis of 9-substituted benzolactam-V8, a class of potent protein kinase C activators, from L-tyrosine through regioselective aromatic nitration, is described (C) 1998 Elsevier Science Ltd. All rights reserved.
• General and Stereospecific Route to 9-Substituted, 8,9-Disubstituted, and 9,10-Disubstituted Analogues of Benzolactam-V8
  作者：Dawei Ma、Wenjun Tang、Alan P. Kozikowski、Nancy E. Lewin、Peter M. Blumberg

  DOI：10.1021/jo990605h

  日期：1999.8.1

  Nitration of the L-tyrosine derivative 9 provides the S-nitro compound 13', which is converted into amide 15 by reduction and protection. Nitration of 15 either ortho or para to the acetamido group gives 16 and 17. After reduction of the nitro group, the anilines 21b and 29b are coupled with triflate 22a, and then cyclized to afford lactams 24 and 31, respectively. By means of a Pd-catalyzed coupling reaction, 8-acetamido-4-decynylbenzolactam-V8 (26) and 9-decyny-10-acctamidobenzolactam-V8 (33) are obtained. The regioisomers 16 and 17 are transformed into a single isomer, 34, which is converted into 9-decynylbenzolactam-V8 (4). The K-i values for 4, 26, and 33 to displace PDBU binding from recombinant PKC alpha (PKC = protein kinase C) art! about 6, 173, and 16 nM. These results demonstrate that while the introduction of a substituent at; either the 8- or 10-position of the 9-substituted benzolactam-V8s lowers their binding affinity, these newly generated analogues still retain reasonably good potency for PKC.
• Role of the Hydrophobic Moiety of Tumor Promoters. Synthesis and Activity of 9-Alkylated Benzolactams.
  作者：Yasuyuki ENDO、Mitsuhiro YAMAGUCHI、Masaaki HIRANO、Koichi SHUDO

  DOI：10.1248/cpb.44.1138

  日期：——

  (-)-Benzolactam-V8-310 reproduces the active conformation and biological activity of teleocidins. Various sizes and shapes of alkyl groups on aromatic nucleus of BL-V8 were synthesized as optically pure forms. Structure-activity results indicate that hydrophobic substituents at C-9 position plays a critical role for the appearance of biological activities.

  (-)-苯内酰胺-V8-310再现了远志素的活性构象和生物活性。在 BL-V8 的芳香核上合成了不同大小和形状的烷基，并以光学纯形式存在。结构-活性结果表明，C-9 位的疏水取代基对生物活性的出现起着关键作用。