2,3,4,5-tetrahydro-1H-2-benzazepine-8-carboxylic acid hydrochloride | 265102-35-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 2,3,4,5-tetrahydro-1H-2-benzazepine-8-carboxylic acid hydrochloride
• 英文别名: 2,3,4,5-tetrahydro-1H-2-benzazepine-8-carboxylicacidhydrochloride；2,3,4,5-tetrahydro-1H-2-benzazepine-8-carboxylic acid;hydrochloride
• CAS: 265102-35-0
• 化学式: C₁₁H₁₃NO₂*ClH
• 分子量: 227.691
• InChiKey: DSMAOIULWDXQEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.84
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  49.3
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3,4,5-tetrahydro-1H-2-benzazepine-8-carboxylic acid hydrochloride 、 9-芴甲基-N-琥珀酰亚胺基碳酸酯 在 碳酸氢钠 作用下， 以 1,4-二氧六环 为溶剂， 生成 2-(9H-Fluoren-9-ylmethoxycarbonyl)-1,3,4,5-tetrahydro-2-benzazepine-8-carboxylic acid
  参考文献：
  名称：

  Identification of a Novel Aminotetralin Class of HDAC6 and HDAC8 Selective Inhibitors

  摘要：

  Herein we report the identification of a novel class of HDAC6 and HDAC8 selective inhibitors through a unique chemistry and phenotypic screening startegy. Tetrahy droisoquinoline 12 was identified as a potent HDAC6 and HDAC8 dual inhibitor from a focussed library through cellular tubulin acetylation and p21 induction screening assays. Scaffold hopping from 12 led to the discovery of an aminotetralin class of HDAC inhibitors. In particular, the 3-R stereoisomeer 32 showed highly potent inhibiton agains HDAC6 and HDAC6 and HDAC8 with IC50 values of 50 and 80 nM, respectively. Treatment of neuroblastoma BE(2) C cells with 32 resulted in elevated levels of acetylated tubulin, TrKA, and neurite outgrowth with only marginal effects on p21 induction and histone H3 acetylation Consistent withits weak enzymatic indhibition of HDAC, showed significantly less cytotoxicity than SAHA and moderately inhibited the growth of myeloma NCI-H929 and OPM-2 cells.

  DOI：

  10.1021/jm5008962
• 作为产物：
  描述：

  8-acetyl-1,3,4,5-tetrahydro-2H-2-benzazepine-2-carbaldehyde 在 盐酸 作用下， 生成 2,3,4,5-tetrahydro-1H-2-benzazepine-8-carboxylic acid hydrochloride
  参考文献：
  名称：

  EP1122252

  摘要：

  公开号：

文献信息

• NITROGENOUS FUSED HETEROCYCLE COMPOUNDS, PROCESS FOR THE PREPARATION THEREOF AND AGENTS CONTAINING THE SAME
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP1122252A1

  公开（公告）日：2001-08-08

  A nitrogen-containing condensed heterocyclic derivative of the present invention, which is a compound represented by the formula: wherein ring A represents benzene ring optionally having a further substituent, -L-represents -O-, -NR3a-, -S-, -SO-, -SO2-, -SO2NR3a-, -SO2NHCONR3a-, -SO2NHC(=NH)NR3a-, -C(=S)-, or -CONR3a- (wherein R3a and R3b represent independently hydrogen atom, cyano group, hydroxy group, amino group, a C1-6 alkyl group or a C1-6 alkoxy group), n represents an integer of 0 to 6, R is hydrogen atom or a hydrocarbon group optionally having a substituent, and may be different in repetition of n, R1 represents a hydrocarbon group optionally having a substituent or a group represented by the formula: (wherein R7 represents a hydrocarbon group optionally having a substituent), R2 represents hydrogen atom, an acyl group, a hydrocarbon group optionally having a substituent or a heterocyclic group optionally having a substituent, X represents a bond, O, S, SO, SO2 or NR4 (wherein R4 represents hydrogen atom, an acyl group or a hydrocarbon group optionally having a substituent), k and m represent independently an integer of 0 to 5, and 1

  本发明的一种含氮缩合杂环衍生物，它是由式表示的化合物： 其中环 A 代表任选具有另一个取代基的苯环，-L-代表-O-，-NR3a-，-S-，-SO-，-SO2-，-SO2NR3a-，-SO2NHCONR3a-，-SO2NHC(＝NH)NR3a-，-C(＝S)-、 或 -CONR3a-（其中 R3a 和 R3b 分别独立地代表氢原子、氰基、羟基、氨基、C1-6 烷基或 C1-6 烷氧基），n 代表 0 至 6 的整数，R 是氢原子或任选具有取代基的烃基，在重复 n 时可以不同，R1 代表任选具有取代基的烃基或由式表示的基团： (其中 R7 代表任选具有取代基的烃基），R2 代表氢原子、酰基、任选具有取代基的烃基或任选具有取代基的杂环基，X 代表键、O、S、SO、SO2 或 NR4（其中 R4 代表氢原子、其中 R4 代表氢原子、酰基或可选具有取代基的烃基），k 和 m 独立地代表 0 至 5 的整数，且 1