1,4-Dihydro-2H-thiochromeno[4,3-c]pyrazol-3-one | 77606-89-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻喃类
• 英文名称: 1,4-Dihydro-2H-thiochromeno[4,3-c]pyrazol-3-one
• 英文别名: 2,4-dihydro-1H-thiochromeno[4,3-c]pyrazol-3-one
• CAS: 77606-89-4
• 化学式: C₁₀H₈N₂OS
• 分子量: 204.252
• InChiKey: KCYJAVFZHACRFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-carbomethoxy-4-thiochromanone 在 溶剂黄146 、 肼 作用下， 反应 10.0h， 以42%的产率得到1,4-Dihydro-2H-thiochromeno[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

文献信息

• Therapeutic [1]benzothiopyrano[4,3-c]pyrazoles
  申请人：The Boots Company PLC

  公开号：EP0354694A1

  公开（公告）日：1990-02-14

  This invention relates to compounds of formula I wherein R₁ represents hydrogen or together with R₂ represents a bond; R₂ together with either one of R₁ and R₃ represents a bond; R₃ represents methyl or together with either one of R₂ and R₄ forms a bond; R₄ represents hydrogen or together with R₃ represents a bond; R₅ represents methyl or ethyl when R₃ together with either one of R₂ and R₄ forms a bond or R₅ represents hydrogen when R₃ represents methyl; R₆ represents hydrogen, halo, trifluoromethyl, a C₁₋₆ alkylthio group, a C₁₋₆ alkyl group or a C₁₋₆ alkoxy group; R₇ represents hydrogen, halo or trifluoromethyl; and R₈ represents hydrogen, halo, trifluoromethyl, hydroxy or a C₁₋₆ alkyl group which have immunomodulatory activity. Compositions containing these compounds and processes to make them are also disclosed.

  这项发明涉及式I的化合物 其中R₁代表氢或与R₂一起代表键；R₂与R₁和R₃中的任一者一起代表键；R₃代表甲基或与R₂和R₄中的任一者一起形成键；R₄代表氢或与R₃一起代表键；R₅代表甲基或乙基，当R₃与R₂和R₄中的任一者一起形成键时，或者R₅代表氢，当R₃代表甲基时；R₆代表氢、卤素、三氟甲基、C₁₋₆烷硫基团、C₁₋₆烷基团或C₁₋₆烷氧基团；R₇代表氢、卤素或三氟甲基；R₈代表氢、卤素、三氟甲基、羟基或具有免疫调节活性的C₁₋₆烷基团。还公开了含有这些化合物的组合物和制备它们的方法。
• Therapeutic agents
  申请人：The Boots Company PLC

  公开号：EP0354693A1

  公开（公告）日：1990-02-14

  This invention relates to compounds of formula I wherein R₁ represents hydrogen or together with R₂ represents a bond; R₂ together with either one of R₁ and R₃ represents a bond; R₃ together with either one of R₂ and R₄ represents a bond; R₄ represents hydrogen or together with R₃ represents a bond; R₅ represents hydrogen or methyl; R₆ represents hydrogen, halo, a C₂₋₆ alkanoyl group, a C₂₋₆ alkoxycarbonyl group, a C₁₋₆ alkylthio group, a C₁₋₆ alkylsulphinyl group, a C₁₋₆ alkylsulphonyl group, carbamoyl, carboxy, or R₅ and R₆ together with the carbon atom to which they are attached represent a cyclopropyl group; R₇ represents hydrogen, halo, trifluoromethyl, methoxy, a C₁₋₆ alkyl group, a C₁₋₆ alkylthio group or a C₁₋₆ alkylsulphinyl group; R₈ represents hydrogen, halo or trifluoromethyl; R₉ and R₁₀, which may be the same or different, each represent halo; or R₉ represents hydrogen and R₁₀ represents hydrogen, halo, trifluoromethyl, hydroxy, nitro, a C₂₋₆ alkanoyloxy group, a C₁₋₆ alkyl group or a C₁₋₆ alkoxy group, which have immunomodulatory activity. Compositions containing these compounds and processes to make them are also disclosed.

  这项发明涉及具有以下结构的化合物，其中R₁代表氢或与R₂一起代表键；R₂与R₁或R₃中的任一者一起代表键；R₃与R₂或R₄中的任一者一起代表键；R₄代表氢或与R₃一起代表键；R₅代表氢或甲基；R₆代表氢、卤素、C₂₋₆烷酰基、C₂₋₆烷氧羰基、C₁₋₆烷基硫基、C₁₋₆烷基砜基、C₁₋₆烷基砜基、氨基甲酰基、羧基，或R₅和R₆与它们连接的碳原子一起代表环丙基；R₇代表氢、卤素、三氟甲基、甲氧基、C₁₋₆烷基、C₁₋₆烷基硫基或C₁₋₆烷基砜基；R₈代表氢、卤素或三氟甲基；R₉和R₁₀，可以相同也可以不同，每个代表卤素；或R₉代表氢，R₁₀代表氢、卤素、三氟甲基、羟基、硝基、C₂₋₆烷酰氧基、C₁₋₆烷基或C₁₋₆烷氧基，具有免疫调节活性。还公开了含有这些化合物的组合物和制备它们的方法。
• Heteroaryl 3-oxo-propanenitrile derivatives and process for their preparation
  申请人：FARMITALIA CARLO ERBA S.r.l.

  公开号：EP0274443B1

  公开（公告）日：1991-05-29
• US4268516A
  申请人：——

  公开号：US4268516A

  公开（公告）日：1981-05-19
• [EN] THERAPEUTIC AGENTS
  申请人：THE BOOTS COMPANY PLC

  公开号：WO1990001481A1

  公开（公告）日：1990-02-22

  (EN) This invention relates to compounds of formula (I), wherein R1 represents hydrogen or together with R2 represents a bond; R2 together with either one of R1 and R3 represents a bond; R3 together with either one of R2 and R4 represents a bond; R4 represents hydrogen or together with R3 represents a bond; R5 represents hydrogen or methyl; R6 represents hydrogen, halo, a C2-6 alkanoyl group, a C2-6 alkoxycarbonyl group, a C1-6 alkylthio group, a C1-6 alkylsulphinyl group, a C1-6 alkylsulphonyl group, carbamoyl, carboxy, or R5 and R6 together with the carbon atom to which they are attached represent a cyclopropyl group; R7 represents hydrogen, halo, trifluoromethyl, methoxy, a C1-6 alkyl group, a C1-6 alkylthio group or a C1-6 alkylsulphinyl group; R8 represents hydrogen, halo or trifluoromethyl; R9 and R10, which may be the same or different, each represent halo; or R9 represents hydrogen and R10 represents hydrogen, halo, trifluoromethyl, hydroxy, nitro, a C2-6 alkanoyloxy group, a C1-6 alkyl group or a C1-6 alkoxy group, which have immunomodulatory activity. Compositions containing these compounds and processes to make them are also disclosed.(FR) Cette invention concerne des composés de formule (I), dans laquelle R1 représente hydrogène ou représente avec R2 une liaison; R2 représente avec R1 ou R3 une liaison, R3 représente avec R2 ou R4 une liaison; R4 représente hydrogène ou représente avec R3 une liaison; R5 représente hydrogène ou méthyle; R6 représente hydrogène, halo, un groupe alcanoyle contenant 2 à 6 atomes de carbone, un groupe alkoxycarbonyle contenant 2 à 6 atomes de carbone, un groupe alkylthio contenant 1 à 6 atomes de carbone, un groupe alkylsulfinyle contenant 1 à 6 atomes de carbone, un groupe alkylsulfonyle contenant 1 à 6 atomes de carbone, carbamoyle, carboxy, ou R5 et R6 représentent avec l'atome de carbone auquel ils sont fixés un groupe cyclopropyle; R7 représente hydrogène, halo, trifluorométhyle, méthoxy, un groupe alkyle contenant 1 à 16 atomes de carbone, un groupe alkylthio contenant 1 à 6 atomes de carbone ou un groupe alkylsulfinyle contenant 1 à 6 atomes de carbone; R8 représente hydrogène, halo ou trifluorométhyle; R9 et R10, pouvant être identiques ou différents, représentent chacun halo; ou R9 représente hydrogène et R10 représente hydrogène, halo, trifluorométhyle, hydroxy, nitro, un groupe alcanoyloxy contenant 2 à 6 atomes de carbone, un groupe alkyle contenant 1 à 16 atomes de carbone ou un groupe alkoxy contenant 1 à 6 atomes de carbone, présentant une activité immunomodulatrice. Sont également décrites des compositions contenant ces composés ainsi que des procédés pour les fabriquer.