4-(2,2-Dioxo-2,3-dihydro-2l6-benzo[1,2,5]thiadiazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester | 473871-19-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 4-(2,2-Dioxo-2,3-dihydro-2l6-benzo[1,2,5]thiadiazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl 4-(2,2-dioxo-1H-2λ6,1,3-benzothiadiazol-3-yl)piperidine-1-carboxylate
• CAS: 473871-19-1
• 化学式: C₁₆H₂₃N₃O₄S
• 分子量: 353.442
• InChiKey: FQYGPBONFZIHPL-UHFFFAOYSA-N

物化性质

• 沸点：
  497.8±55.0 °C(Predicted)
• 密度：
  1.306±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  87.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(2,2-Dioxo-2,3-dihydro-2l6-benzo[1,2,5]thiadiazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester 在 盐酸 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 生成 1-[1-(1,3,-dihydroinden-2-yl)-4-piperidinyl]-2,1,3-benzothiadiazol-2,2-dione
  参考文献：
  名称：

  1,3-Dihydro-2,1,3-benzothiadiazol-2,2-diones and 3,4-dihydro-1H-2,1,3-benzothidiazin-2,2-diones as ligands for the NOP receptor

  摘要：

  A series of 1,3-dihydro-2,1,3-benzothiadiazol-2,2-diones (1) and 3,4-dihydro-1H-2,1,3-benzothidiazin-2,2-diones (II) were prepared. While the five-member ring series (I) did not show good affinity for opioid receptors, the six-member ring series (II) exhibited extremely high affinity and selectivity for the NOP receptor and showed full agonist activity, as determined by stimulation of GTPgamma[S-35] binding. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.08.001
• 作为产物：
  描述：

  4-(2-氨基苯氨基)哌啶-1-甲酸叔丁酯 在 磺酰胺 作用下， 以 二乙二醇二甲醚 为溶剂， 生成 4-(2,2-Dioxo-2,3-dihydro-2l6-benzo[1,2,5]thiadiazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Rapid access towards follow-up NOP receptor agonists using a knowledge based approach

  摘要：

  A knowledge based approach has been adopted to identify novel NOP receptor agonists with simplified hydrophobes. Substitution of the benzimidazol-2-one piperidine motif with a range of hydrophobic groups and pharmacophore guided bio-isosteric replacement of the benzimidazol-2-one moiety was explored. Compound 51 was found to be a high affinity, potent NOP receptor agonist with reduced affinity for the hERG channel. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.09.028

文献信息

• Quinolinone derivatives and their use to treat pain
  申请人：EURO-CELTIQUE S.A.

  公开号：EP1997818A2

  公开（公告）日：2008-12-03

  A compound of the having the general formula (I) or general formula (II) wherein Z, A, B, C, R1, R2, Q1 and W1 and n are as described herein.

  具有通式（I）或通式（II）的化合物，其中 Z、A、B、C、R1、R2、Q1 和 W1 及 n 如本文所述。
• NOCICEPTIN ANALOGS
  申请人：Goehring R. Richard

  公开号：US20090253727A1

  公开（公告）日：2009-10-08

  A compound of the having the general formula (I) or general formula (II): wherein Z, A, B, C, R 1 , R 2 , Q, W, and n are as described herein.
• US7563809B2
  申请人：——

  公开号：US7563809B2

  公开（公告）日：2009-07-21
• Rapid access towards follow-up NOP receptor agonists using a knowledge based approach
  作者：Ronald Palin、John K. Clark、Louise Evans、Helen Feilden、Dan Fletcher、Niall M. Hamilton、Andrea K. Houghton、Philip S. Jones、Duncan McArthur、Brian Montgomery、Paul D. Ratcliffe、Alasdair R.C. Smith、Aaron Sutherland、Mark A. Weston、Grant Wishart

  DOI：10.1016/j.bmcl.2009.09.028

  日期：2009.11

  A knowledge based approach has been adopted to identify novel NOP receptor agonists with simplified hydrophobes. Substitution of the benzimidazol-2-one piperidine motif with a range of hydrophobic groups and pharmacophore guided bio-isosteric replacement of the benzimidazol-2-one moiety was explored. Compound 51 was found to be a high affinity, potent NOP receptor agonist with reduced affinity for the hERG channel. (C) 2009 Elsevier Ltd. All rights reserved.
• 1,3-Dihydro-2,1,3-benzothiadiazol-2,2-diones and 3,4-dihydro-1H-2,1,3-benzothidiazin-2,2-diones as ligands for the NOP receptor
  作者：R. Richard Goehring、John F.W. Whitehead、K. Brown、Khondaker Islam、Xin Wen、Xiaoming Zhou、Zhengming Chen、Kenneth J. Valenzano、Wendy S. Miller、Shen Shan、Donald J. Kyle

  DOI：10.1016/j.bmcl.2004.08.001

  日期：2004.10

  A series of 1,3-dihydro-2,1,3-benzothiadiazol-2,2-diones (1) and 3,4-dihydro-1H-2,1,3-benzothidiazin-2,2-diones (II) were prepared. While the five-member ring series (I) did not show good affinity for opioid receptors, the six-member ring series (II) exhibited extremely high affinity and selectivity for the NOP receptor and showed full agonist activity, as determined by stimulation of GTPgamma[S-35] binding. (C) 2004 Elsevier Ltd. All rights reserved.