tert-butyl 4-(5-amino-2-(4-chlorophenyl)thiazolo[5,4-d]pyrimidin-7-yl)piperazine-1-carboxylate | 1262120-86-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: tert-butyl 4-(5-amino-2-(4-chlorophenyl)thiazolo[5,4-d]pyrimidin-7-yl)piperazine-1-carboxylate
• 英文别名: Tert-butyl 4-[5-amino-2-(4-chlorophenyl)-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazine-1-carboxylate
• CAS: 1262120-86-4
• 化学式: C₂₀H₂₃ClN₆O₂S
• 分子量: 446.961
• InChiKey: VYIJWRNIVMCTGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  126
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-(5-amino-2-(4-chlorophenyl)thiazolo[5,4-d]pyrimidin-7-yl)piperazine-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以88%的产率得到2-(4-chlorophenyl)-7-(piperazin-1-yl)thiazolo[5,4-d]pyrimidin-5-amine
  参考文献：
  名称：

  Discovery of 7-N-Piperazinylthiazolo[5,4-d]pyrimidine Analogues as a Novel Class of Immunosuppressive Agents with in Vivo Biological Activity

  摘要：

  Herein we describe the synthesis and in vitro and in vivo activity of thiazolo[5,4-d]pyrimidines as a novel class of immunosuppressive agents, useful for preventing graft rejection after organ transplantation. This research resulted in the discovery of a series of compounds with potent activity in the mixed lymphocyte reaction (MLR) assay, which is well-known as the in vitro model for in vivo rejection after organ transplantation. The most potent congeners displayed IC50 values of less than 50 nM in this MLR assay and hence are equipotent to cyclosporin A, a clinically used immunosuppressive drug. One representative of this series was further evaluated in a preclinical animal model of organ transplantation and showed excellent in vivo efficacy. It validates these compounds as new promising immunosuppressive drugs.

  DOI：

  10.1021/jm101254z
• 作为产物：
  描述：

  tert-butyl 4-(2,5-diamino-6-chloropyrimidin-4-yl)piperazine-1-carboxylate 在 sodium sulphide nonahydrate 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 生成 tert-butyl 4-(5-amino-2-(4-chlorophenyl)thiazolo[5,4-d]pyrimidin-7-yl)piperazine-1-carboxylate
  参考文献：
  名称：

  Discovery of 7-N-Piperazinylthiazolo[5,4-d]pyrimidine Analogues as a Novel Class of Immunosuppressive Agents with in Vivo Biological Activity

  摘要：

  Herein we describe the synthesis and in vitro and in vivo activity of thiazolo[5,4-d]pyrimidines as a novel class of immunosuppressive agents, useful for preventing graft rejection after organ transplantation. This research resulted in the discovery of a series of compounds with potent activity in the mixed lymphocyte reaction (MLR) assay, which is well-known as the in vitro model for in vivo rejection after organ transplantation. The most potent congeners displayed IC50 values of less than 50 nM in this MLR assay and hence are equipotent to cyclosporin A, a clinically used immunosuppressive drug. One representative of this series was further evaluated in a preclinical animal model of organ transplantation and showed excellent in vivo efficacy. It validates these compounds as new promising immunosuppressive drugs.

  DOI：

  10.1021/jm101254z

文献信息

• Discovery of 7-<i>N</i>-Piperazinylthiazolo[5,4-<i>d</i>]pyrimidine Analogues as a Novel Class of Immunosuppressive Agents with in Vivo Biological Activity
  作者：Mi-Yeon Jang、Yuan Lin、Steven De Jonghe、Ling-Jie Gao、Bart Vanderhoydonck、Mathy Froeyen、Jef Rozenski、Jean Herman、Thierry Louat、Kristien Van Belle、Mark Waer、Piet Herdewijn

  DOI：10.1021/jm101254z

  日期：2011.1.27

  Herein we describe the synthesis and in vitro and in vivo activity of thiazolo[5,4-d]pyrimidines as a novel class of immunosuppressive agents, useful for preventing graft rejection after organ transplantation. This research resulted in the discovery of a series of compounds with potent activity in the mixed lymphocyte reaction (MLR) assay, which is well-known as the in vitro model for in vivo rejection after organ transplantation. The most potent congeners displayed IC50 values of less than 50 nM in this MLR assay and hence are equipotent to cyclosporin A, a clinically used immunosuppressive drug. One representative of this series was further evaluated in a preclinical animal model of organ transplantation and showed excellent in vivo efficacy. It validates these compounds as new promising immunosuppressive drugs.