Methyl 3-amino-4-(methoxymethoxy)benzoate | 873852-28-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Methyl 3-amino-4-(methoxymethoxy)benzoate
• CAS: 873852-28-9
• 化学式: C₁₀H₁₃NO₄
• 分子量: 211.218
• InChiKey: SXNRFYPGUOQGMI-UHFFFAOYSA-N

物化性质

• 沸点：
  364.5±32.0 °C(Predicted)
• 密度：
  1.196±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  70.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 Methyl 3-amino-4-(methoxymethoxy)benzoate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 以5.28 g的产率得到N,N-3-(dimethylamino)-4-(methoxymethyl)benzoic acid methyl ester
  参考文献：
  名称：

  Small molecules that protect against β-amyloid-induced cytotoxicity by inhibiting aggregation of β-amyloid

  摘要：

  Aggregated beta-amyloid (A beta) plays crucial roles in Alzheimer's disease (AD) pathogenesis, therefore blockade of Ab aggregation is considered as a potential therapeutic target. We designed and synthesized small molecules to reduce A beta-induced cytotoxicity by inhibiting A beta aggregation. The small molecules were screened via ThT, MTT, and cell-based cytotoxicity assay (A beta burden assay). Selected compounds 1c, 1d, 1e, and 1f were then investigated by evaluating their effects on cognitive impairment of acute AD mice model. Learning and memory dysfunction by injection of A beta(1-42) was recovered by administration of these molecules. Especially, 1d showed the best recovery activity in Y-maze task, object recognition task, and passive avoidance task with dose dependent manner. These results suggest that 1d has high potential as a therapeutic agent for AD. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.06.045
• 作为产物：
  描述：

  4-羟基-3-硝基苯甲酸 在 硫酸 、 palladium 10% on activated carbon 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 Methyl 3-amino-4-(methoxymethoxy)benzoate
  参考文献：
  名称：

  Small molecules that protect against β-amyloid-induced cytotoxicity by inhibiting aggregation of β-amyloid

  摘要：

  Aggregated beta-amyloid (A beta) plays crucial roles in Alzheimer's disease (AD) pathogenesis, therefore blockade of Ab aggregation is considered as a potential therapeutic target. We designed and synthesized small molecules to reduce A beta-induced cytotoxicity by inhibiting A beta aggregation. The small molecules were screened via ThT, MTT, and cell-based cytotoxicity assay (A beta burden assay). Selected compounds 1c, 1d, 1e, and 1f were then investigated by evaluating their effects on cognitive impairment of acute AD mice model. Learning and memory dysfunction by injection of A beta(1-42) was recovered by administration of these molecules. Especially, 1d showed the best recovery activity in Y-maze task, object recognition task, and passive avoidance task with dose dependent manner. These results suggest that 1d has high potential as a therapeutic agent for AD. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.06.045

文献信息

• 3-Aminobenzamide compounds and inhibitors of vanilloid receptor subtype 1 (VR1) activity
  申请人：Koga Yoshihisa

  公开号：US20060035939A1

  公开（公告）日：2006-02-16

  The present invention relates to a novel 3-aminobenzamide compound represented by the following formula which effectively inhibits vanilloid receptor subtype 1 (VR1) activity (wherein, for example, R 1 is a C1-6 alkyl group which may be substituted, R 2 is a hydrogen atom, a C1-6 alkyl group or a C1-6 alkoxy group which may be substituted, R 3 is a hydrogen atom or a C1-6 alkyl group, R 4 is a C1-6 alkyl group, a C1-6 alkoxy group, or a halo C1-6 alkyl group, m is an integer of 1 to 5 and P is a carbon or hetero ring) or a pharmaceutically acceptable salt thereof. The pharmaceutical composition comprising as active ingredients the 3-aminobenzamide compound or a pharmaceutically acceptable salt thereof is useful for treating diseases involved in VR1 activity such as pain, acute pain, chronic pain, neuropathic pain, rheumatoid arthritis pain, and neuralgia.

  本发明涉及一种新型3-氨基苯甲酰胺化合物，其由以下公式表示，有效抑制辣椒素受体亚型1（VR1）的活性（其中，例如，R1是可能被取代的C1-6烷基基团，R2是氢原子、C1-6烷基基团或可能被取代的C1-6烷氧基团，R3是氢原子或C1-6烷基基团，R4是C1-6烷基基团、C1-6烷氧基团或卤代的C1-6烷基基团，m是1到5的整数，P是碳或杂环）或其药学上可接受的盐。包含作为活性成分的3-氨基苯甲酰胺化合物或其药学上可接受的盐的药物组合物对于治疗涉及VR1活性的疾病，如疼痛、急性疼痛、慢性疼痛、神经病性疼痛、类风湿性关节炎疼痛和神经痛，是有用的。
• 3-AMINOBENZAMIDE COMPOUNDS AND VANILLOID RECEPTOR SUBTYPE 1 (VR1) INHIBITORS
  申请人：KOGA YOSHIHISA

  公开号：US20100022523A1

  公开（公告）日：2010-01-28

  The present invention relates to a novel 3-aminobenzamide compound represented by the following formula which effectively inhibits vanilloid receptor subtype 1 (VR1) activity (wherein, for example, R 1 is a C1-6 alkyl group which may be substituted, R 2 is a hydrogen atom, a C1-6 alkyl group or a C1-6 alkoxy group which may be substituted, R 3 is a hydrogen atom or a C1-6 alkyl group, R 4 is a C1-6 alkyl group, a C1-6 alkoxy group, or a halo C1-6 alkyl group, m is an integer of 1 to 5 and P is a carbon or hetero ring) or a pharmaceutically acceptable salt thereof. The pharmaceutical composition comprising as active ingredients the 3-aminobenzamide compound or a pharmaceutically acceptable salt thereof is useful for treating diseases involved in VR1 activity such as pain, acute pain, chronic pain, neuropathic pain, rheumatoid arthritis pain, and neuralgia.

  本发明涉及一种新型3-氨基苯酰胺化合物，其化学式如下，能够有效抑制vanilloid受体亚型1（VR1）的活性（其中，例如，R1是C1-6烷基，可以被取代，R2是氢原子，C1-6烷基或C1-6烷氧基，可以被取代，R3是氢原子或C1-6烷基，R4是C1-6烷基，C1-6烷氧基或卤代C1-6烷基，m是1到5的整数，P是碳或杂环）。该药物组合物包括3-氨基苯酰胺化合物或其药学上可接受的盐作为活性成分，对于治疗VR1活性相关的疾病，如疼痛、急性疼痛、慢性疼痛、神经性疼痛、类风湿性关节炎疼痛和神经痛等具有益处。
• 3-AMINOBENAMIDE COMPOUND AND VANILLOID RECEPTOR 1 (VR1) ACTIVITY INHIBITOR
  申请人：Japan Tobacco, Inc.

  公开号：EP1775283A1

  公开（公告）日：2007-04-18

  The present invention relates to a novel 3-aminobenzamide compound represented by the following formula which effectively inhibits vanilloid receptor subtype 1 (VR1) activity (wherein, for example, R1 is a C1-6 alkyl group which may be substituted, R2 is a hydrogen atom, a C1-6 alkyl group or a C1-6 alkoxy group which may be substituted, R3 is a hydrogen atom or a C1-6 alkyl group, R4 is a C1-6 alkyl group, a C1-6 alkoxy group, or a halo C1-6 alkyl group, m is an integer of 1 to 5 and P is a carbon or hetero ring) or a pharmaceutically acceptable salt thereof. The pharmaceutical composition comprising as active ingredients the 3-aminobenzamide compound or a pharmaceutically acceptable salt thereof is useful for treating diseases involved in VR1 activity such aspain, acutepain, chronicpain, neuropathic pain, rheumatoid arthritis pain, and neuralgia.

  本发明涉及一种由下式表示的新型3-氨基苯甲酰胺化合物，它能有效地抑制类香草素受体亚型1（VR1）的活性（其中，例如，R1是可被取代的C1-6烷基，R2是氢原子、R3 是氢原子或 C1-6 烷基，R4 是 C1-6 烷基、C1-6 烷氧基或卤代 C1-6 烷基，m 是 1 至 5 的整数，P 是碳环或杂环）或其药学上可接受的盐。包含作为活性成分的 3-氨基苯甲酰胺化合物或其药学上可接受的盐的药物组合物可用于治疗涉及 VR1 活性的疾病，如阿斯匹灵、急性阿斯匹灵、慢性阿斯匹灵、神经性疼痛、风湿性关节炎疼痛和神经痛。