2-[4-(氨基甲基)苯氧基]乙酸 | 33321-38-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-[4-(氨基甲基)苯氧基]乙酸
• 英文名称: 4-(aminomethyl)-phenoxyacetic acid
• 英文别名: 4-aminomethylphenoxyacetic acid；4-(Aminomethyl)-phenoxyessigsaeure；4-Aminomethylphenoxyessigsaeure；2-[4-(Azaniumylmethyl)phenoxy]acetate
• CAS: 33321-38-9
• 化学式: C₉H₁₁NO₃
• 分子量: 181.191
• InChiKey: BTFJMWHBYNEKIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  72.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[4-(氨基甲基)苯氧基]乙酸 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  有效和选择性脯氨酸衍生的二肽基肽酶IV抑制剂。

  摘要：

  对Merck样品的内部筛选表明，脯氨酸衍生的高苯丙氨酸3作为DPP-IV抑制剂具有中等效力（DPP-IV IC50 = 1.9 microM）。对3的优化导致化合物37，它是迄今为止发现的最有效和选择性最强的DPP-IV抑制剂之一。

  DOI：

  10.1016/j.bmcl.2004.07.056

文献信息

• [EN] ALKYNYL ARYL CARBOXAMIDES<br/>[FR] ALKYNYLARYL-CARBOXAMIDES
  申请人：APPLIED RESEARCH SYSTEMS

  公开号：WO2005012280A1

  公开（公告）日：2005-02-10

  The present invention is related to alkynyl aryl carboxamides of Formula (I’) and use thereof for the treatment and/or prevention of an inflammatory disorder, obesity and/or metabolic disorders mediated by insulin resistance or hyperglycemia, comprising diabetes type I and/or II, inadequate glucose tolerance. insulin resistance, hyperlipidemia, hypertriglyceridemia- hypercholesterolemia, polycystic ovary syndrome (PCOS). In particular, the present invention is related to the use of alkynyl aryl carboxamides of Formula (I’) to modulate, notably to inhibit the activity of PTPs. (I’) A is a C2-C15 alkynyl, C2-C6-alkynyl aryl, C2-C6-alkynyl heteroaryl. Cy is an aryl, heteroaryl, cycloalkyl or heterocycle group; n is either 0 or 1. Cy' is an aryl., which may optionally be fused by a 3-8 membered cycloalkyl. R1and R2 are independently from each other is selected from the group consisting of hydrogen or (CI-C6)alkyl. R4and R5 are each independently from each other selected from the group consisting of H, hydroxy. C1 -C6 alkyl, carboxy, C1-C6 alkoxy, C1 -C3 alkyl carboxy, C2-C3 alkenyl carboxy, C2-C3 alkynyl carboxy, amino or R4 and R5 may form an unsaturated or saturated heterocyclic ring, whereby at least one of R4 or R5 is not a hydrogen or C1-C6 alkyl.

  本发明涉及式(I')的炔基芳基羧酰胺及其用于治疗和/或预防由胰岛素抵抗或高血糖介导的炎症疾病、肥胖和/或代谢紊乱的使用，包括I型和/或II型糖尿病、葡萄糖耐量不足、胰岛素抵抗、高脂血症、高甘油三酯血症-高胆固醇血症、多囊卵巢综合征(PCOS)。特别是，本发明涉及使用式(I')的炔基芳基羧酰胺来调节，尤其是抑制PTPs的活性。(I') A是C2-C15炔基，C2-C6-炔基芳基，C2-C6-炔基杂芳基。Cy是芳基、杂芳基、环烷基或杂环族；n是0或1。Cy'是一个芳基，它可以选择性地通过一个3-8成员的环烷基融合。R1和R2独立地互选自由氢或(C1-C6)烷基组成的组。R4和R5各自独立地互选自H、羟基。C1-C6烷基、羧基、C1-C6烷氧基、C1-C3烷基羧基、C2-C3烯基羧基、C2-C3炔基羧基、氨基或R4和R5可以形成一个不饱和或饱和的杂环，其中至少R4或R5不是氢或C1-C6烷基。
• [EN] ARYL DICARBOXAMIDES<br/>[FR] ARYL-DICARBOXAMIDES
  申请人：APPLIED RESEARCH SYSTEMS

  公开号：WO2005011685A1

  公开（公告）日：2005-02-10

  The present invention is related to aryl dicarboxamides of formula (I) and use thereof for the treatment and/or prevention of obesity and/or metabolic disorders mediated by insulin resistance or hyperglycernia, comprising diabetes type I and/or II, inadequate glucose tolerance, insulin resistance, hyperlipidemia, hypertriglyceridemia, hypercholes-terolemia, polycystic ovary syndrome (PCOS). In particular, the present invention is related to the use of aryl dicarboxamides of formula (I) to modulate, notably to inhibit the activity of PTPs. A is an airninocarbonyl moiety; Cy is an aryl, heteroaryl, aryl-heteroaryl, heteroaryl-aryl, aryl-aryl, cycloalkyl or heterocycle group; n is either 0 or 1; R1 and R2 are independently from each other is selected from the group consisting of hydrogen or C1-C6-alkyl; R4 and R5 are each independently from each other selected from the group consisting of H, hydroxy, C1-C6 alkyl, carboxy, C1-C6 alkoxy, C1-C3 alkyl carboxy, C2-C3 alkenyl carboxy, C2-C3 alkynyl carboxy, amino or R4 and R5 may form an unsaturated or saturated heterocyclic ring, whereby at least one of R4 or R5 is not a hydrogen or C1-C6 alkyl.

  本发明涉及式(I)的芳基二羧酰胺及其用于治疗和/或预防肥胖和/或由胰岛素抵抗或高血糖介导的代谢紊乱的使用，包括I型和/或II型糖尿病、葡萄糖耐量不足、胰岛素抵抗、高脂血症、高甘油三酯血症、高胆固醇血症、多囊卵巢综合征(PCOS)。特别是，本发明涉及使用式(I)的芳基二羧酰胺调节，尤其是抑制PTPs的活性。A是氨基甲酰基团；Cy是芳基、杂芳基、芳基-杂芳基、杂芳基-芳基、芳基-芳基、环烷基或杂环组；n为0或1；R1和R2独立地选自由氢或C1-C6-烷基组成的组；R4和R5各自独立地选自由H、羟基、C1-C6烷基、羧基、C1-C6烷氧基、C1-C3烷基羧基、C2-C3烯基羧基、C2-C3炔基羧基、氨基组成的组，或者R4和R5可以形成一个不饱和或饱和的杂环，其中至少R4或R5不是氢或C1-C6烷基。
• Bicyclic beta-lactam carboxylic acids
  申请人：Ciba-Geigy Corporation

  公开号：US04965260A1

  公开（公告）日：1990-10-23

  Compounds of the formula ##STR1## in which R.sub.1 is lower alkyl substituted by hydroxy or by protected hydroxy, R.sub.2 represents carboxy or functionally modified carboxy, R.sub.3 is hydrogen, amino, mono- or di-substituted amino, carbamoyl, hydroxy, protected hydroxy, carbamoyloxy, lower alkoxy, halogen, lower alkanoyl, sulphamoyl or heteroarylthio, each of R.sub.4 and R.sub.5, independently of the other, represents hydrogen, lower alkyl, hydroxy, protected hydroxy, lower alkoxy, halogen, amino, protected amino, lower alkanoylamino or carbamoyl, or R.sub.4 and R.sub.5 together represent methylenedioxy, Y represents a group of the formula --O--, --S-- or --NR.sub.6 --, R.sub.6 is hydrogen or lower alkyl, A.sub.1 represents lower alkylene or unsubstituted or substituted phenylene and A.sub.2 represents a direct bond or lower alkylene, and salts of such compounds, have antibacterial activity. The compounds of the formula I are manufactured by processes that are known per se.

  公式为##STR1##的化合物，其中R.sub.1是被羟基或保护羟基取代的低烷基，R.sub.2代表羧基或功能修饰的羧基，R.sub.3是氢、氨基、单取代或双取代氨基、氨基甲酰、羟基、保护羟基、羟基甲酰氧基、低烷氧基、卤素、低烷酰基、磺酰氨基或杂环硫基，R.sub.4和R.sub.5中的每一个，独立于另一个，代表氢、低烷基、羟基、保护羟基、低烷氧基、卤素、氨基、保护氨基、低烷酰氨基或氨基甲酰，或者R.sub.4和R.sub.5一起代表亚甲二氧基，Y代表--O--、--S--或--NR.sub.6 --的式团，R.sub.6是氢或低烷基，A.sub.1代表低烷基或未取代或取代的苯基，A.sub.2代表直接键或低烷基，以及这类化合物的盐，具有抗菌活性。公式I的化合物是通过已知的方法制造的。
• Discovery of β-aminoacyl containing thiazolidine derivatives as potent and selective dipeptidyl peptidase IV inhibitors
  作者：Woul Seong Park、Seung Kyu Kang、Mi Ae Jun、Mi Sik Shin、Ki Young Kim、Sang Dal Rhee、Myung Ae Bae、Min Sun Kim、Kwang Rok Kim、Nam Sook Kang、Sung-eun Yoo、Jie Oh Lee、Dong Hyun Song、Peter Silinski、Stephen Edward Schneider、Jin Hee Ahn、Sung Soo Kim

  DOI：10.1016/j.bmcl.2011.01.041

  日期：2011.3

  containing thiazolidine derivatives was synthesized and evaluated for their ability to inhibit DPP-IV. Several thiazolidine derivatives with an acid moiety were found to be potent DPP-IV inhibitors. Among them, compound 2da is the most active in this series with an IC50 value of 1 nM, and it showed excellent selectivity over DPP-IV related enzymes including DPP-2, DPP-8, and DPP-9. Compound 2da is chemically

  合成了一系列含有β-氨基酰基的噻唑烷衍生物，并评估了它们抑制DPP-IV的能力。发现具有酸部分的几种噻唑烷衍生物是有效的DPP-IV抑制剂。其中，化合物2da是该系列中活性最高的化合物，IC 50值为1 nM，与DPP-IV相关的酶（包括DPP-2，DPP-8和DPP-9）相比，具有出色的选择性。化合物2da具有化学和代谢稳定性，未显示CYP抑制，hERG结合或细胞毒性。化合物2db（2da的酯类前药）在大鼠和狗模型中口服后显示出良好的体内DPP-IV抑制作用。
• Selective MMP-13 inhibitors
  申请人：Klingler Otmar

  公开号：US20050004111A1

  公开（公告）日：2005-01-06

  The invention relates to a pyrimidine-4,6-dicarboxylic acid diamide compound, pharmaceutical preparation comprising it, process for preparing it and method for its pharmaceutical use. Particularly, the pyrimidine-4,6-dicarboxylic acid diamide compound is useful for selectively inhibiting collagenase matrix metalloproteinase (MMP) 13, or for treating a degenerative joint disease.

  该发明涉及一种嘧啶-4,6-二羧酸二酰胺化合物，包括该化合物的药物制剂，制备该化合物的方法以及该化合物的药用方法。特别是，嘧啶-4,6-二羧酸二酰胺化合物可用于选择性抑制胶原酶基质金属蛋白酶（MMP）13，或用于治疗退行性关节疾病。