(Z)-3-(1-methylpyrrolidin-2-ylidene)-3H-indole | 4631-10-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (Z)-3-(1-methylpyrrolidin-2-ylidene)-3H-indole
• 英文别名: 3-(1-methyl-2-pyrrolidinylidene)-3H-indole；3-(1-methylpyrrolidin-2-ylidene)-3H-indole；3-(1-methyl-pyrrolidin-2-ylidene)-3H-indole；3-<1-Methyl-2-pyrrolidinyliden>-3H-indol；3-(1-Methyl-2-pyrridinyliden)3H-indol；3-(N-Methyl-2-pyrrolidinyl)indol；(3Z)-3-(1-methyl-2-pyrrolidinylidene)-3H-indole；(3Z)-3-(1-methylpyrrolidin-2-ylidene)indole
• CAS: 4631-10-1
• 化学式: C₁₃H₁₄N₂
• 分子量: 198.268
• InChiKey: HNNADWWHLOZSTI-ACCUITESSA-N

物化性质

• 熔点：
  229-231 °C
• 沸点：
  340.5±42.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  15.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-3-(1-methylpyrrolidin-2-ylidene)-3H-indole 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以83%的产率得到3-(1-甲基-2-吡咯烷基)-1H-吲哚
  参考文献：
  名称：

  Selective Inhibition of Histone Deacetylase 10: Hydrogen Bonding to the Gatekeeper Residue is Implicated

  摘要：

  The discovery of isozyme-selective histone deacetylase (HDAC) inhibitors is critical for understanding the biological functions of individual HDACs and for validating HDACs as drug targets. The isozyme HDAC10 contributes to chemotherapy resistance and has recently been described to be a polyamine deacetylase, but no studies toward selective HDAC10 inhibitors have been published. Using two complementary assays, we found Tubastatin A, an HDAC6 inhibitor, to potently bind HDAC10. We synthesized Tubastatin A derivatives and found that a basic amine in the cap group was required for strong HDAC10 binding. HDAC10 inhibitors mimicked knockdown by causing dose-dependent accumulation of acidic vesicles in a neuroblastoma cell line. Furthermore, docking into human HDAC10 homology models indicated that a hydrogen bond between a cap group nitrogen and the gatekeeper residue Glu272 was responsible for potent HDAC10 binding. Taken together, our data provide an optimal platform for the development of HDAC10-selective inhibitors, as exemplified with the Tubastatin A scaffold.

  DOI：

  10.1021/acs.jmedchem.8b01936
• 作为产物：
  描述：

  3-pyrrolidin-2-ylidene-3H-indole 生成 (Z)-3-(1-methylpyrrolidin-2-ylidene)-3H-indole
  参考文献：
  名称：

  Ahuja, Padma; Singh, Jujhar; Anand, Nitya, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1983, vol. 22, # 8, p. 723 - 724

  摘要：

  DOI：

文献信息

• Al-Khawaja, Ibtisam; Beddoes, Roy L.; Bishop, David I., Journal of Chemical Research, Miniprint, 1984, # 9, p. 2738 - 2767
  作者：Al-Khawaja, Ibtisam、Beddoes, Roy L.、Bishop, David I.、Cernic, Robert J.、Joule, John A.、Mills, Owen S.

  DOI：——

  日期：——
• Bishop, David I.; Al-Khawaja, Ibtisam K.; Heatley, Frank, Journal of Chemical Research, Miniprint, 1982, # 6, p. 1766 - 1776
  作者：Bishop, David I.、Al-Khawaja, Ibtisam K.、Heatley, Frank、Joule, John A.

  DOI：——

  日期：——
• Bishop, David I.; Al-Khawaja, Ibtisam K.; Joule, John A., Journal of Chemical Research, Miniprint, 1981, # 12, p. 4279 - 4290
  作者：Bishop, David I.、Al-Khawaja, Ibtisam K.、Joule, John A.

  DOI：——

  日期：——
• BISHOP, D. I.;AL-KHAWAJA, I. K.;JOULE, J. A., J. CHEM. RES. MICROFICHE, 1981, N 12, 361
  作者：BISHOP, D. I.、AL-KHAWAJA, I. K.、JOULE, J. A.

  DOI：——

  日期：——
• BISHOP, D. I.;AL-KHAWAJA, IBTISAM, K.;HEATLEY, F.;JOULE, J. A., J. CHEM. RES. MICROFICHE, 1982, N 6, 159
  作者：BISHOP, D. I.、AL-KHAWAJA, IBTISAM, K.、HEATLEY, F.、JOULE, J. A.

  DOI：——

  日期：——