6-<<(chloroacetyl)amino>methyl>-7-hydroxy-4-methyl-1-indanone | 103234-37-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 6-<<(chloroacetyl)amino>methyl>-7-hydroxy-4-methyl-1-indanone
• 英文别名: 4-methyl-6-α-chloroacetylaminomethyl-7-hydroxy-1-indanone；6-chloroacetylaminomethyl-2,3-dihydro-7-hydroxy-4-methyl-1H-indene-1-one；4-Methyl-6-alpha-chloroacetylaminomethyl-7-hydroxy-1-indanone；2-chloro-N-[(4-hydroxy-7-methyl-3-oxo-1,2-dihydroinden-5-yl)methyl]acetamide
• CAS: 103234-37-3
• 化学式: C₁₃H₁₄ClNO₃
• 分子量: 267.712
• InChiKey: HRCMAYGMWJRORI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-<<(chloroacetyl)amino>methyl>-7-hydroxy-4-methyl-1-indanone 在 platinum(IV) oxide 盐酸羟胺 、 氢气 、 potassium carbonate 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 3.0h， 生成 3-Amino-5-aminomethyl-7-methyl-indan-4-ol
  参考文献：
  名称：

  具有中枢神经系统刺激活性的新型脑保护剂。2.1-（酰基氨基）-7-羟基茚满衍生物的合成和药理作用。

  摘要：

  在不断寻找具有中枢神经系统（CNS）刺激活性的新型脑保护药物时，已合成了一系列1-（酰基氨基）-7-羟基茚满衍生物，并对其双重活性进行了测试。根据其对低氧条件下（210 mmHg）小鼠存活的影响，评估了该系列化合物的脑保护活性，并通过评估其对脑震荡引起的昏迷恢复的促进作用，检查了其对中枢神经系统的刺激活性。在小鼠中。几种化合物以30 mg / kg po的剂量延长了低氧条件下小鼠的存活率。该系列中的四种化合物在相同剂量下均表现出CNS刺激作用。其中，7-羟基-1-[[4-（3-甲氧基苯基）-1-哌嗪基]乙酰基]氨基] -2,2,4,6-四甲基茚满（18，OPC-14117），

  DOI：

  10.1021/jm00111a014
• 作为产物：
  描述：

  氯乙酰胺-N-甲醇 、 7-羟基-4-甲基-1-茚酮 在 硫酸 作用下， 以80%的产率得到6-<<(chloroacetyl)amino>methyl>-7-hydroxy-4-methyl-1-indanone
  参考文献：
  名称：

  具有中枢神经系统刺激活性的新型脑保护剂。2.1-（酰基氨基）-7-羟基茚满衍生物的合成和药理作用。

  摘要：

  在不断寻找具有中枢神经系统（CNS）刺激活性的新型脑保护药物时，已合成了一系列1-（酰基氨基）-7-羟基茚满衍生物，并对其双重活性进行了测试。根据其对低氧条件下（210 mmHg）小鼠存活的影响，评估了该系列化合物的脑保护活性，并通过评估其对脑震荡引起的昏迷恢复的促进作用，检查了其对中枢神经系统的刺激活性。在小鼠中。几种化合物以30 mg / kg po的剂量延长了低氧条件下小鼠的存活率。该系列中的四种化合物在相同剂量下均表现出CNS刺激作用。其中，7-羟基-1-[[4-（3-甲氧基苯基）-1-哌嗪基]乙酰基]氨基] -2,2,4,6-四甲基茚满（18，OPC-14117），

  DOI：

  10.1021/jm00111a014

文献信息

• 2,3-dihydro-1H-indene derivatives
  申请人：Otsuka Pharmaceutical Co., Ltd.

  公开号：US05242919A1

  公开（公告）日：1993-09-07

  Novel 2,3-dihydro-1H-indene derivatives and salts thereof represented by the general formula (1), ##STR1## [wherein R.sup.1 and R.sup.2 are each a hydrogen atom, a lower alkyl group, a phenyl group which may have halogen atoms and/or alkyl groups as the substituents on the phenyl ring; R.sup.3 is a halgoen atom or a lower alkyl group; R.sup.4 is a hydrogen atom, a halogen atom, a phenyl-lower alkyl group, a cycloalkyl-lower alkyl group or the like; R.sup.5 is a hydroxyimino group, an alkylamino group or a group of the formula --NHR.sup.8 (wherein R.sup.8 is a hydrogen atom, a halogen-substituted lower alkanoyl group or the like); R.sup.6 is a hydrogen atom or a phenyl group; and R.sup.7 is a hydrogen atom or a lower alkyl group]. The 2,3-dihydro-1H-indene derivatives and salt thereof are useful as improving agents for treating anoxemic and hypoxic symptoms and syndromes accompanied therewith, cerebral activators, amnesia curvative agents, presbyophrenia curvative agents, treating agents for breathing arrest and improving agents for hypoxia accompanied with potassium cyanide poisoning, as well as useful an anti-inflammatory agents and hypotensive agents.

  一种由通式（1）表示的新颖的2,3-二氢-1H-茚衍生物及其盐，其中：##STR1## [其中R.sup.1和R.sup.2均为氢原子，较低的烷基，苯基，其苯环上可能有卤原子和/或烷基作为取代基；R.sup.3为卤原子或较低的烷基；R.sup.4为氢原子，卤原子，苯基-较低烷基，环烷基-较低烷基或类似物；R.sup.5为羟肟基，烷基氨基或公式--NHR.sup.8的基团（其中R.sup.8为氢原子，卤代较低脂肪酰基或类似物）；R.sup.6为氢原子或苯基；R.sup.7为氢原子或较低的烷基]。2,3-二氢-1H-茚衍生物及其盐可作为改善治疗缺氧和低氧症状和综合症的剂量，脑活化剂，改善失忆症的剂量，老年痴呆症的治疗剂量，呼吸停止的治疗剂量和改善氰化钾中毒伴随的低氧症的剂量，以及有用的抗炎剂和降压剂。
• 1-amino-2,3-dihydro-1H-indene compounds
  申请人：Otsuka Pharmaceutical Co., Ltd.

  公开号：US04788130A1

  公开（公告）日：1988-11-29

  Novel 2,3-dihydro-1H-indene derivatives and salts thereof represented by the general formula (1), ##STR1## [wherein R.sup.1 and R.sup.2 are each a hydrogen atom, a lower alkyl group, a phenyl group which may have halogen atoms and/or alkyl groups as the substituents on the phenyl ring; R.sup.3 is a halogen atom or a lower alkyl group; R.sup.4 is a hydrogen atom, a halogen atom, a phenyl-lower alkyl group, a cycloalkyl-lower alkyl group or the like; R.sup.5 is a hydroxyimino group, an alkylamino group or a group of the formula --NHR.sup.8 (wherein R.sup.8 is a hydrogen atom, a halogen-substituted lower alkanoyl group or the like); R.sup.6 is a hydrogen atom or a phenyl group; and R.sup.7 is a hydrogen atom or a lower alkyl group]. The 2,3-dihydro-1H-indene derivatives and salt thereof are useful as improving agents for treating anoxemic and hypoxic symptoms and syndromes accompanied therewith, cerebral activators, amnesia curative agents, presbyophrenia curative agents, treating agents for breathing arrest and improving agents for hypoxia accompanied with potassium cyanide poisoning, as well as useful as anti-inflammatory agents and hypotensive agents.

  通式（1）所表示的新型2,3-二氢-1H-茚衍生物及其盐，其中R1和R2分别是氢原子、较低的烷基、苯基，苯环上可能带有卤原子和/或烷基取代基；R3是卤原子或较低的烷基；R4是氢原子、卤原子、苯基-较低烷基、环烷-较低烷基或类似基团；R5是羟亚胺基、烷基氨基或式--NHR8的基团（其中R8是氢原子、卤代较低酰基或类似基团）；R6是氢原子或苯基；R7是氢原子或较低的烷基。这些2,3-二氢-1H-茚衍生物及其盐可用作改善缺氧和低氧症状和伴随症候群的治疗剂、脑活化剂、改善失忆症的药剂、老年痴呆症的治疗剂、呼吸停止的治疗剂和改善伴随钾氰化物中毒的低氧症的药剂，以及作为抗炎剂和降压剂。
• Indane derivatives and salts thereof
  申请人：Otsuka Pharmaceutical Co., Ltd.

  公开号：US04792628A1

  公开（公告）日：1988-12-20

  Indane derivatives and their salts represented by the general formula (1), ##STR1## wherein R.sup.1 is an amino group which may have lower alkyl groups as the substituents, a hydroxylimino group, an alkanoylamino group having 1 to 10 carbon atoms which may have halogen atoms as the substituents, a lower alkylsulfonylamino group, a phenylsulfonylamino group which may have lower alkyl groups as the substituents on the phenyl ring, a benzoylamino group having lower alkyl groups as the substituents on the phenyl ring, and a phenyl-lower alkylamino group having a hydroxyl groups or a lower alkyl groups as the substituents on the phenyl ring, R.sup.2 is a hydrogen atom, a lower alkyl group, a halogen atom, a nitro group, an amino group, an amino-lower alkyl group, a lower alkanoylamino group, a lower alkanoylamino-lower alkyl group which may have halogen atoms as the substituents, a lower alkylthio group, a 1-piperidinesulfonyl group, or a lower alkenyl group; R.sup.3 is a hydrogen atom, a lower alkyl group, or a halogen atom; R.sup.4 and R.sup.5 are the same or different from each other, and are each a hydrogen atom, or a lower alkyl group; provided that when R.sup.1 is a hydroxylimino group, then R.sup.2 and R.sup.3 should not be hydrogen atoms at the same time. The indane derivatives and their salts are useful as preventive and curative agents for various diseases and disorders caused by the excessive formation and accumulation of the active oxygen radicals and the peroxidized substances in the living body, and/or the defects of phylaxis mechanisms of the living body, for example anti-arreriosclerotic agents, carcinogenesis preventive agents, carcinostatic agents, anti-inflammatory agents, analgesics, autoimmune disease curative agents, platelets aggregation inhibitory agents, hypotensive agents, anti-hyperlipemic agents, retinosis of immature infant and cataract preventive and curative agents. The indane derivatives and their salts are also useful as antioxidants for oils and fats being contained in processed foods.

  Indane衍生物及其盐的一般式表示为（1），其中R.sup.1是氨基团，其可以具有较低的烷基取代基，羟基亚胺基，具有1到10个碳原子的脂肪酰胺基，其可以具有卤素原子作为取代基，较低的烷基磺酰胺基，苯基磺酰胺基，其可以具有苯环上的较低烷基取代基，苯甲酰胺基，其在苯环上具有较低烷基取代基，以及苯基-较低烷基氨基基，其中苯环上具有羟基或较低烷基取代基，R.sup.2是氢原子，较低烷基基团，卤素原子，硝基基团，氨基团，氨基-较低烷基基团，脂肪酰胺基，其可以具有卤素原子作为取代基，较低烷基硫基，1-哌啶磺酰基或较低烯基基团; R.sup.3是氢原子，较低烷基基团或卤素原子; R.sup.4和R.sup.5相同或不同，均为氢原子或较低烷基基团; 前提是当R.sup.1为羟基亚胺基时，R.sup.2和R.sup.3不能同时为氢原子。这些Indane衍生物及其盐可用作预防和治疗各种疾病和障碍的药剂，这些疾病和障碍是由于活性氧自由基和过氧化物质在生物体内的过度形成和积累以及生物体的免疫机制缺陷引起的，例如抗动脉粥样硬化药剂，癌症预防药剂，抗癌药剂，抗炎药，止痛药，自身免疫疾病治疗药剂，血小板聚集抑制剂，降压剂，抗高脂血症药剂，未成熟婴儿视网膜病和白内障预防和治疗药剂。这些Indane衍生物及其盐还可用作加工食品中所含油脂的抗氧化剂。
• 2,3-dihydro-1H-indene derivatives and their use as pharmaceutical agents
  申请人：Otsuka Pharmaceutical Co., Ltd.

  公开号：US05055474A1

  公开（公告）日：1991-10-08

  Novel 2,3-dihydro-1H-indene derivatives and salts thereof represented by the general formula (1), ##STR1## [wherein R.sup.1 and R.sup.2 are each a hydrogen atom, a lower alkyl group, a phenyl group which may have halogen atoms and/or alkyl groups as the substituents on the phenyl ring; R.sup.3 is a halogen atom or a lower alkyl group; R.sup.4 is a hydrogen atom, a halogen atom, a phenyl-lower alkyl group, a cycloalkyl-lower alkyl group or the like; R.sup.5 is a hydroxyimino group, an alkylamino group or a group of the formula --NHR.sup.8 (wherein R.sup.8 is a hydrogen atom, a halogen-substituted lower alkanoyl group or the like); R.sup.6 is a hydrogen atom or a phenyl group; and R.sup.7 is a hydrogen atom or a lower alkyl group]. The 2,3-dihydro-1H-indene derivatives and salt thereof are useful as improving agents for treating anoxemic and hypoxic symptoms and syndromes accompanied therewith, cerebral activators, amnesia curative agents, presbyophrenia curative agents, treating agents for breathing arrest and improving agents for hypoxia accompanied with potassium cyanide poisoning, as well as useful as anti-inflammatory agents and hypotensive agents.

  通式（1）所表示的新型2,3-二氢-1H-茚衍生物及其盐，其中R1和R2分别是氢原子、低碳基、苯基，苯环上可能有卤素基团和/或烷基基团作为取代基；R3是卤素原子或低碳基；R4是氢原子、卤素原子、苯基-低碳基、环烷基-低碳基或类似物；R5是羟肟基、烷基氨基或公式--NHR8的基团（其中R8是氢原子、卤素取代的低碳酰基基团或类似物）；R6是氢原子或苯基；R7是氢原子或低碳基。这些2,3-二氢-1H-茚衍生物及其盐可作为改善缺氧和低氧症状和综合征的治疗剂、脑活化剂、改善记忆障碍的治疗剂、老年痴呆症的治疗剂、呼吸骤停的治疗剂和改善氰化钾中毒引起的低氧症状的治疗剂，以及作为抗炎剂和降压剂使用。
• 2,3-Dihydro-1H-indene derivatives, a process for preparing them and pharmaceutical compositions containing same
  申请人：OTSUKA PHARMACEUTICAL CO., LTD.

  公开号：EP0173331B1

  公开（公告）日：1991-08-14