2-(4-chlorophenyl)-1,2,3,4-tetrahydro[1]benzothiopyrano[4,3-c]pyrazol-3-one-5-oxide | 77606-94-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(4-chlorophenyl)-1,2,3,4-tetrahydro[1]benzothiopyrano[4,3-c]pyrazol-3-one-5-oxide
• 英文别名: 2-(4-chlorophenyl)-5-oxo-1,4-dihydrothiochromeno[4,3-c]pyrazol-3-one
• CAS: 77606-94-1
• 化学式: C₁₆H₁₁ClN₂O₂S
• 分子量: 330.795
• InChiKey: IZODXSVAHHNGPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  68.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-chlorophenyl)-1,2,3,4-tetrahydro[1]benzothiopyrano[4,3-c]pyrazol-3-one-5-oxide 在 盐酸 作用下， 以 溶剂黄146 为溶剂， 反应 3.5h， 以64%的产率得到2-(P-chlorophenyl)-2,3-dihydro<1>benzothiopyrano<4,3-c>pyrazol-3-one
  参考文献：
  名称：

  Novel immunosuppressive agents. Potent immunological activity of some benzothiopyrano[4,3-c]pyrazol-3-ones

  摘要：

  A unique class of immunosuppressive agents has been found be the use of a mouse model of immunity. A number of bensothiopyrano[4,3-c]pyrazol-3-ones are potent inhibitors of both the humoral and cellular immune response developed in mice in response to El4 tumor cells. These compounds exhibit a selectivity for inhibiting the humoral response. Structure-activity relationships and Hansch analyses of data from the mouse model are discussed. One of the most potent compounds, 2-(4'-chlorophenyl)bensothiopyrano[4,3-c]pyrazol-3-one (1, CP-17 193), exhibits ED50 values for inhibiting the humoral and cellular responses in the range of 0.5-2 mg/kg, po, in the mouse model and also inhibits antibody production to several other antigens and prolongs skin graft survival in mice. These compounds are shown in several ways to be distinct from the lymphocytotoxic drugs cyclophosphamide and azathioprine.

  DOI：

  10.1021/jm00139a012
• 作为产物：
  描述：

  3-carbomethoxy-4-thiochromanone 在 双氧水 、 溶剂黄146 作用下， 以 溶剂黄146 为溶剂， 反应 5.5h， 生成 2-(4-chlorophenyl)-1,2,3,4-tetrahydro[1]benzothiopyrano[4,3-c]pyrazol-3-one-5-oxide
  参考文献：
  名称：

  Novel immunosuppressive agents. Potent immunological activity of some benzothiopyrano[4,3-c]pyrazol-3-ones

  摘要：

  A unique class of immunosuppressive agents has been found be the use of a mouse model of immunity. A number of bensothiopyrano[4,3-c]pyrazol-3-ones are potent inhibitors of both the humoral and cellular immune response developed in mice in response to El4 tumor cells. These compounds exhibit a selectivity for inhibiting the humoral response. Structure-activity relationships and Hansch analyses of data from the mouse model are discussed. One of the most potent compounds, 2-(4'-chlorophenyl)bensothiopyrano[4,3-c]pyrazol-3-one (1, CP-17 193), exhibits ED50 values for inhibiting the humoral and cellular responses in the range of 0.5-2 mg/kg, po, in the mouse model and also inhibits antibody production to several other antigens and prolongs skin graft survival in mice. These compounds are shown in several ways to be distinct from the lymphocytotoxic drugs cyclophosphamide and azathioprine.

  DOI：

  10.1021/jm00139a012

文献信息

• [1]Benzothiopyrano[4,3-c]pyrazoles as immunoregulatory agents
  申请人：Pfizer Inc.

  公开号：US04268516A1

  公开（公告）日：1981-05-19

  1,2,3,4-Tetrahydrobenzothiopyrano[4,3-c]pyrazol-3-ones and 2,3-dihydro[1]benzothiopyrano[4,3-c]pyrazol-3-ones, of respective structure I and II, ##STR1## wherein n is an integer of value from 0 to 2; R is phenyl; phenyl monosubstituted with chloro, bromo, fluoro, methyl, methoxy, nitro or trifluoromethyl; or phenyl disubstituted with chloro; and X is hydrogen or chloro; are described. These novel compounds are immunoregulators which, through suppression of the immune response in mammals, are useful in inhibiting rejection of organ transplants, as well as in the therapy of auto-immune diseases.

  1,2,3,4-四氢苯并硫吡喃[4,3-c]吡唑-3-酮和2,3-二氢[1]苯并硫吡喃[4,3-c]吡唑-3-酮，具有结构I和II，其中n是取值范围为0至2的整数；R是苯基；苯基单取代物为氯、溴、氟、甲基、甲氧基、硝基或三氟甲基；或苯基双取代物为氯；X是氢或氯。这些新颖化合物是免疫调节剂，通过抑制哺乳动物的免疫反应，在抑制器官移植排斥以及治疗自身免疫疾病方面具有用途。
• LOMBARDINO, J. G.;OTTERNESS, I. G.;MUREN, J. F.
  作者：LOMBARDINO, J. G.、OTTERNESS, I. G.、MUREN, J. F.

  DOI：——

  日期：——
• US4268516A
  申请人：——

  公开号：US4268516A

  公开（公告）日：1981-05-19
• Novel immunosuppressive agents. Potent immunological activity of some benzothiopyrano[4,3-c]pyrazol-3-ones
  作者：Joseph G. Lombardino、Ivan G. Otterness

  DOI：10.1021/jm00139a012

  日期：1981.7

  A unique class of immunosuppressive agents has been found be the use of a mouse model of immunity. A number of bensothiopyrano[4,3-c]pyrazol-3-ones are potent inhibitors of both the humoral and cellular immune response developed in mice in response to El4 tumor cells. These compounds exhibit a selectivity for inhibiting the humoral response. Structure-activity relationships and Hansch analyses of data from the mouse model are discussed. One of the most potent compounds, 2-(4'-chlorophenyl)bensothiopyrano[4,3-c]pyrazol-3-one (1, CP-17 193), exhibits ED50 values for inhibiting the humoral and cellular responses in the range of 0.5-2 mg/kg, po, in the mouse model and also inhibits antibody production to several other antigens and prolongs skin graft survival in mice. These compounds are shown in several ways to be distinct from the lymphocytotoxic drugs cyclophosphamide and azathioprine.