3-(4-bromobutyl)-5,5-dimethyl-4-thiazolidinone | 124468-46-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 3-(4-bromobutyl)-5,5-dimethyl-4-thiazolidinone
• 英文别名: 3-(4-bromobutyl)-5,5-dimethyl-1,3-thiazolidin-4-one
• CAS: 124468-46-8
• 化学式: C₉H₁₆BrNOS
• 分子量: 266.202
• InChiKey: ICNBNRPSZGXSDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  45.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(1-哌嗪)-1H-吲唑 、 3-(4-bromobutyl)-5,5-dimethyl-4-thiazolidinone 以 N-甲基乙酰胺 为溶剂， 生成 3-(4-(1-[1H-indazol-3-yl]-4-piperazinyl)-butyl)-5,5-dimethyl-4-thiazolidinone
  参考文献：
  名称：

  3-[1-thiazolidinylbutyl-4-piperazinyl]-1H-indazoles

  摘要：

  该发明涉及式的3-[1-噻唑烷基-4-哌嗪基]-1H-吲唑醇 ##STR1##，其中R.sub.1和R.sub.2分别独立地为氢或低烷基，或R.sub.1和R.sub.2与它们连接的碳原子一起形成环戊烷、环己烷或环庚烷环；R.sub.3和R.sub.4独立地为氢或低烷基，或R.sub.3和R.sub.4与它们连接的碳原子一起形成环戊烷、环己烷或环庚烷环；R.sub.5为氢、低烷基、烷酰基或芳酰基；X为氢、卤素、低烷基或烷氧基；m为1到3的整数，其药学上可接受的酸盐及必要时的光学、几何和立体异构体和混合物。该发明的化合物可用作抗精神病药物。

  公开号：

  US05041445A1
• 作为产物：
  描述：

  3-(4-bromobutyl)-4-thiazolidinone 、 碘甲烷 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 生成 3-(4-bromobutyl)-5,5-dimethyl-4-thiazolidinone
  参考文献：
  名称：

  与[3- [4- [4-（6-氟代苯并[b]噻吩-3-基] -1-哌嗪基]丁基] -2,5]相关的一系列新型（哌嗪基丁基）噻唑烷酮类抗精神病药的结构活性关系， 5-三甲基-4-噻唑烷酮马来酸酯。

  摘要：

  HP-236（3- [4- [4-（6-氟苯并[b]噻吩-3-基）-1-哌嗪基]丁基] -2,5,5-三甲基-4-噻唑烷酮马来酸酯； P-9236） （54）显示了潜在的非典型抗精神病药活性的药理学特征。制备了与该化合物结构相关的一系列哌嗪基丁基丁基噻唑烷酮，并在体外评估了多巴胺D2和5-羟色胺5HT2和5HT1A受体的亲和力。在具有潜在抗精神病活性的动物模型中对化合物进行了体内检查，并在预测锥体束外副作用（EPS）责任的模型中进行了筛选。描述了这些化合物的合成，其结构-活性关系的详细信息以及新的先导化合物50的发现，以及化合物50和54的分布图的进一步发展。

  DOI：

  10.1021/jm960268u

文献信息

• 3-[4-(1-substituted-4-piperazinyl)butyl]-4-thiazolidinone and related
  申请人：Hoechst-Roussel Pharmaceuticals Incorporated

  公开号：US05229388A1

  公开（公告）日：1993-07-20

  There are disclosed compounds of the formula, ##STR1## where n is 0, 1 or 2; A is ##STR2## where X in each occurrence is independently hydrogen, halogen, loweralkyl, hydroxy, nitro, loweralkoxy, amino, cyano, trifluoromethyl or methylthio; Y in each occurrence is independently hydrogen, halogen, loweralkyl, hydroxy, nitro, loweralkoxy, amino, cyano, trifluoromethyl or methylthio; m is 1 or 2; k is 1 or 2; R.sub.1 and R.sub.2 are independently hydrogen, loweralkyl, ##STR3## or aryl except that when R.sub.1 is ##STR4## or aryl, R.sub.2 is hydrogen, or alternatively R.sub.1 +R.sub.2 taken together with the carbon atom to which they are attached form a cyclopentane, cyclohexane, cycloheptane, pyran, thiopyran, indan or piperidine ring; R.sub.3 and R.sub.4 are independently hydrogen or loweralkyl, or alternatively R.sub.3 +R.sub.4 taken together with the carbon atom to which they are attached form a cyclopentane, cyclohexane, cycloheptane, pyran, thiopyran, pyrrolidine or piperidine ring, the term aryl signifying an unsubstituted phenyl group or a phenyl group substituted with 1, 2 or 3 substituents each of which being independently loweralkyl, loweralkoxy, hydroxy, halogen, loweralkylthio, cyano, amino or trifluoromethyl, which are useful as antipsychotic, analgesic, anticonvulsant and anxiolytic agents.

  公式中披露了化合物，其中n为0、1或2；A为其中X在每次出现时独立地为氢、卤素、较低烷基、羟基、硝基、较低烷氧基、氨基、氰基、三氟甲基或甲硫基；Y在每次出现时独立地为氢、卤素、较低烷基、羟基、硝基、较低烷氧基、氨基、氰基、三氟甲基或甲硫基；m为1或2；k为1或2；R.sub.1和R.sub.2独立地为氢、较低烷基、或芳基，但当R.sub.1为或芳基时，R.sub.2为氢，或者R.sub.1 +R.sub.2与它们附着的碳原子一起形成环戊烷、环己烷、环庚烷、吡喃、硫代吡喃、茚或哌啶环；R.sub.3和R.sub.4独立地为氢或较低烷基，或者R.sub.3 +R.sub.4与它们附着的碳原子一起形成环戊烷、环己烷、环庚烷、吡喃、硫代吡喃、吡咯烷或哌啶环，术语芳基表示未取代的苯基或一个苯基，其上取代基为1、2或3个，每个取代基独立地为较低烷基、较低烷氧基、羟基、卤素、较低烷硫基、氰基、氨基或三氟甲基，这些化合物可用作抗精神病、镇痛、抗癫痫和抗焦虑药物。
• 3-[4-(1-Substituted-4-piperazinyl)butyl]-4-thiazolidinone compounds
  申请人：Hoechst-Roussel Pharmaceuticals Inc.

  公开号：US04933453A1

  公开（公告）日：1990-06-12

  3-[4-1-substituted-4-piperazinyl)butyl]-4-thiazolidinone compounds which are useful as antipsychotic, analgesic, anticonvulsant and anxiolytic agents.

  3-[4-（1-取代-4-哌嗪基）丁基]-4-噻唑烷酮化合物可用作抗精神病药、镇痛药、抗抽搐药和抗焦虑药。
• 3-[4-(1-substituted-4-piperazinyl)butyl]-4-thiazolidinone compounds
  申请人：Hoechst-Roussel Pharmaceuticals Inc.

  公开号：US05037984A1

  公开（公告）日：1991-08-06

  There are disclosed compounds of the formula ##STR1## where n is 0 or 1; A is ##STR2## where X in each occurrence is independently hydrogen, halogen, loweralkyl hydroxy, nitro, loweralkoxy, amino, cyano, trifluoromethyl or methylthio; Y in each occurrence is independently hydrogen, halogen, loweralkyl, hydroxy, nitro, loweralkoxy, amino, cyano, trifluoromethyl or methylthio; m is 1 or 2; k is 1 or 2; R.sub.1 and R.sub.2 are independently hydrogen, loweralkyl, ##STR3## or aryl except that when R.sub.1 is ##STR4## or aryl, R.sub.2 is hydrogen, or alternatively R.sub.1 +R.sub.2 taken together with the carbon atom to which they are attached form a cyclopentane, cyclohexane, cycloheptane, pyran, thiopyran, indan or piperidine ring; R.sub.3 and R.sub.4 are independently hydrogen or loweralkyl, or alternatively R.sub.3 +R.sub.4 taken together with the carbon atom to which they are attached form a cyclopentane, cyclohexane, cycloheptane, pyran, thiopyran, pyrrolidine or piperidine ring, the term aryl signifying an unsubstituted phenyl group or a phenyl group substituted with 1, 2 or 3 substituents each of which being independently loweralkyl, loweralkoxy, hydroxy, halogen, loweralkythio, cyano, amino or trifluoromethyl, which are useful as antipsychotic, analgesic, anticonvulsant and anxiolytic agents.

  公开了化合物的式子##STR1##其中n为0或1; A为##STR2##其中每个X独立地为氢、卤素、低碳基羟基、硝基、低碳基氧基、氨基、氰基、三氟甲基或甲硫基;每个Y独立地为氢、卤素、低碳基、羟基、硝基、低碳基氧基、氨基、氰基、三氟甲基或甲硫基;m为1或2;k为1或2;R.sub.1和R.sub.2独立地为氢、低碳基、##STR3##或芳基，但当R.sub.1为##STR4##或芳基时，R.sub.2为氢，或者R.sub.1+R.sub.2与它们附着的碳原子一起形成环戊烷、环己烷、环庚烷、吡喃、硫代吡喃、茚烷或哌啶环;R.sub.3和R.sub.4独立地为氢或低碳基，或者R.sub.3+R.sub.4与它们附着的碳原子一起形成环戊烷、环己烷、环庚烷、吡喃、硫代吡喃、吡咯烷或哌啶环，术语芳基表示未取代的苯基或取代了1、2或3个基团的苯基，每个基团独立地为低碳基、低碳氧基、羟基、卤素、低碳硫基、氰基、氨基或三氟甲基，这些化合物可用作抗精神病、镇痛、抗癫痫和抗焦虑药物。
• 3-<4-substituted-4-piperazinyl)buty]-4-thiazolidinone and related
  申请人：Hoechst-Roussel Pharmaceuticals Inc.

  公开号：US05371087A1

  公开（公告）日：1994-12-06

  There are disclosed compounds of the formula, ##STR1## where n is 0, 1 or 2; A is ##STR2## where X in each occurrence is independently hydrogen, halogen, loweralkyl, hydroxy, nitro, loweralkoxy, amino, cyano, trifluoromethyl or methylthio; Y in each occurrence is independently hydrogen, halogen, loweralkyl, hydroxy, nitro, loweralkoxy, amino cyano, trifluoromethyl or methylthio; m is 1 or 2; k is 1 or 2; R.sub.1 and R.sub.2 are independently hydrogen, loweralkyl, ##STR3## or aryl except that when R.sub.1 is ##STR4## or aryl, R.sub.2 is hydrogen, or alternatively R.sub.1 +R.sub.2 taken together with the carbon atom to which they are attached form a cyclopentane, cyclohexane, cycloheptane, pyran, thiopyran, indan or piperidine ring; R.sub.3 and R.sub.4 are independently hydrogen or loweralkyl, or alternatively R.sub.3 +R.sub.4 taken together with the carbon atom to which they are attached form a cyclopentane, cyclohexane, cycloheptane, pyran, thiopyran, pyrrolidine or piperidine ring, the term aryl signifying an unsubstituted phenyl group or a phenyl group substituted with 1, 2 or 3 substituents each of which being independently loweralkyl, loweralkoxy, hydroxy, halogen, loweralkylthio, cyano, amino or trifluoromethyl, which are useful as antipsychotic, analgesic, anticonvulsant and anxiolytic agents.

  公开了化合物的公式，其中n为0、1或2；A为##STR2##其中每次出现的X独立地为氢、卤素、低烷基、羟基、硝基、低烷氧基、氨基、氰基、三氟甲基或甲硫基；每次出现的Y独立地为氢、卤素、低烷基、羟基、硝基、低烷氧基、氨基、氰基、三氟甲基或甲硫基；m为1或2；k为1或2；R.sub.1和R.sub.2独立地为氢、低烷基、##STR3##或芳基，但当R.sub.1为##STR4##或芳基时，R.sub.2为氢，或者R.sub.1+R.sub.2与它们附着的碳原子共同形成环戊烷、环己烷、环庚烷、吡喃、硫代吡喃、茚烷或哌啶环；R.sub.3和R.sub.4独立地为氢或低烷基，或者R.sub.3+R.sub.4与它们附着的碳原子共同形成环戊烷、环己烷、环庚烷、吡喃、硫代吡喃、吡咯烷或哌啶环，术语芳基表示未取代的苯基或取代有1、2或3个取代基的苯基，每个取代基独立地为低烷基、低烷氧基、羟基、卤素、低烷硫基、氰基、氨基或三氟甲基，这些化合物可用作抗精神病、镇痛、抗癫痫和抗焦虑剂。
• 3-(4-substituted-4-piperazinyl)butyl-4-thiazolidinone and related
  申请人：Hoechst-Roussel Pharmaceuticals Inc.

  公开号：US05136037A1

  公开（公告）日：1992-08-04

  There are disclosed compounds of the formula, ##STR1## where n is 0 or 1; A is ##STR2## where X in each occurrence is independently hydrogen, halogen, loweralkyl, hydroxy, nitro, loweralkoxy, amino, cyano, trifluoromethyl or methylthio; Y in each occurrence is independently hydrogen, halogen, loweralkyl, hydroxy, nitro, loweralkoxy, amino, cyano, trifluoromethyl or methylthio; m is 1 or 2; k is 1 or 2; R.sub.1 and R.sub.2 are independently hydrogen, lower alkyl, ##STR3## or alternatively R.sub.1 +R.sub.2 taken together with the carbon atom to which they are attached form a cyclopentane, cyclohexane, cycloheptane, pyran, thiopyran, indan or piperidine ring; R.sub.3 and R.sub.4 are independently hydrogen or loweralkyl, or alternatively R.sub.3 +R.sub.4 taken together with the carbon atom to which they are attached form a cyclopentane, cyclohexane, cycloheptane, pyran, thiopyran, pyrrolidine or piperidine ring, the term aryl signifying an unsubstituted phenyl group or a phenyl group substituted with 1, 2 or 3 substituents each of which being independently loweralkyl, loweralkoxy, hydroxy, halogen, loweralkylthio, cyano, amino or trifluoromethyl, which are useful as antipsychotic, analgesic, anticonvulsant and anxiolytic agents.

  公开了化合物的公式，其中n为0或1；A为##STR2##其中每个X独立地是氢，卤素，低碳基，羟基，硝基，低碳氧基，氨基，氰基，三氟甲基或甲硫基；每个Y在出现时独立地是氢，卤素，低碳基，羟基，硝基，低碳氧基，氨基，氰基，三氟甲基或甲硫基；m为1或2；k为1或2；R.sub.1和R.sub.2独立地是氢，低碳基，##STR3##或者R.sub.1+R.sub.2与它们附着的碳原子结合形成环戊烷，环己烷，环庚烷，吡喃，硫代吡喃，茚烷或哌啶环；R.sub.3和R.sub.4独立地是氢或低碳基，或者R.sub.3+R.sub.4与它们附着的碳原子结合形成环戊烷，环己烷，环庚烷，吡喃，硫代吡喃，吡咯烷或哌啶环，术语芳基表示未取代的苯基或取代有1、2或3个取代基的苯基，每个取代基都是独立的低碳基，低碳氧基，羟基，卤素，低碳硫基，氰基，氨基或三氟甲基，这些化合物是作为抗精神病，镇痛，抗惊厥和抗焦虑剂使用的。