(±)-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)methanol | 35811-51-9

• 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: (±)-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)methanol
• 英文别名: 6-Chlor-1,2,3,4-tetrahydrocarbazol-2-methanol；6-chloro-1,2,3,4-tetrahydrocarbazole-2-methanol；(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)methanol
• CAS: 35811-51-9
• 化学式: C₁₃H₁₄ClNO
• 分子量: 235.713
• InChiKey: NNXJUWHZIUSTPV-UHFFFAOYSA-N

物化性质

• 沸点：
  425.1±40.0 °C(Predicted)
• 密度：
  1.315±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  36
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-羰基-1-环己羧酸 在 lithium aluminium tetrahydride 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 (±)-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)methanol
  参考文献：
  名称：

  Bacterial Sliding Clamp Inhibitors that Mimic the Sequential Binding Mechanism of Endogenous Linear Motifs

  摘要：

  The bacterial DNA replication machinery presents new targets for the development of antibiotics acting via novel mechanisms. One such target is the protein-protein interaction between the DNA sliding clamp and the conserved peptide linear motifs in DNA polymerases. We previously established that binding of linear motifs to the Escherichia coli sliding clamp occurs via a sequential mechanism that involves two subsites (I and II). Here, we report the development of small-molecule inhibitors that mimic this mechanism. The compounds contain tetrahydrocarbazole moieties as "anchors" to occupy subsite I. Functional groups appended at the tetrahydrocarbazole nitrogen bind to a channel gated by the side chain of M362 and lie at the edge of subsite II. One derivative induced the formation of a new binding pocket, termed subsite III, by rearrangement of a loop adjacent to subsite I. Discovery of the extended binding area will guide further inhibitor development.

  DOI：

  10.1021/acs.jmedchem.5b00232

文献信息

• Cyclopenta[b]indole-2-carboxylic acids and derivatives thereof
  申请人：Hoffmann-La Roche Inc.

  公开号：US04009181A1

  公开（公告）日：1977-02-22

  1,2,3,4-Tetrahydrocarbazoles and cyclopenta[b] indoles prepared from the corresponding phenyl hydrazines and corresponding cyclohexanones or cyclopentanones, respectively, are described. The products of the invention are useful anti-inflammatory, analgesic and anti-rheumatic agents.

  本发明描述了由相应的苯基肼和相应的环己酮或环戊酮制备的1,2,3,4-四氢咔唑和环戊[b]吲哚。本发明的产物是有用的抗炎、镇痛和抗风湿药物。
• US4009181A
  申请人：——

  公开号：US4009181A

  公开（公告）日：1977-02-22
• Bacterial Sliding Clamp Inhibitors that Mimic the Sequential Binding Mechanism of Endogenous Linear Motifs
  作者：Zhou Yin、Louise R. Whittell、Yao Wang、Slobodan Jergic、Cong Ma、Peter J. Lewis、Nicholas E. Dixon、Jennifer L. Beck、Michael J. Kelso、Aaron J. Oakley

  DOI：10.1021/acs.jmedchem.5b00232

  日期：2015.6.11

  The bacterial DNA replication machinery presents new targets for the development of antibiotics acting via novel mechanisms. One such target is the protein-protein interaction between the DNA sliding clamp and the conserved peptide linear motifs in DNA polymerases. We previously established that binding of linear motifs to the Escherichia coli sliding clamp occurs via a sequential mechanism that involves two subsites (I and II). Here, we report the development of small-molecule inhibitors that mimic this mechanism. The compounds contain tetrahydrocarbazole moieties as "anchors" to occupy subsite I. Functional groups appended at the tetrahydrocarbazole nitrogen bind to a channel gated by the side chain of M362 and lie at the edge of subsite II. One derivative induced the formation of a new binding pocket, termed subsite III, by rearrangement of a loop adjacent to subsite I. Discovery of the extended binding area will guide further inhibitor development.