2,5-二甲基苯氧基乙酸 | 7356-41-4

• 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: 2,5-二甲基苯氧基乙酸
• 英文名称: 2,5-dimethylphenoxyacetic acid
• 英文别名: (2,5-Dimethyl-phenoxy)-essigsaeure；2-(2,5-dimethylphenoxy)acetic acid
• CAS: 7356-41-4
• 化学式: C₁₀H₁₂O₃
• mdl: MFCD00014356
• 分子量: 180.203
• InChiKey: RSJMMLSDGNQOEO-UHFFFAOYSA-N

物化性质

• 熔点：
  114-116°C
• 稳定性/保质期：
  遵照规格使用和储存则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• 海关编码：
  2918990090
• 包装等级：
  III
• 危险类别：
  8
• 危险性防范说明：
  P264,P270,P273,P280,P301+P312+P330,P305+P351+P338+P310,P501
• 危险品运输编号：
  3261
• 危险性描述：
  H302,H318,H412
• 储存条件：
  密封在阴凉干燥的环境中。

反应信息

• 作为反应物：
  描述：

  2,5-二甲基苯氧基乙酸 在 lithium hydroxide 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 rac-(SR)-[(5SR)-1-(2,6-dichlorobenzyl)-2-oxo-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-5-yl]-(2,5-dimethylphenoxy)acetic acid
  参考文献：
  名称：

  Novel Benzo[1,4]diazepin-2-one Derivatives as Endothelin Receptor Antagonists

  摘要：

  Since its discovery in 1988 by Yanagisawa et al., endothelin (ET), a potent vasoconstrictor, has been widely implicated in the pathophysiology of cardiovascular, cerebrovascular, and renal diseases. Many research groups have embarked on the discovery and development of ET receptor antagonists for the treatment of such diseases. While several compounds, e.g., ambrisentan 2, are in late clinical trials for various indications, one compound (bosentan, Tracleer) is being marketed to treat pulmonary arterial hypertension. Inspired by the structure of ambrisentan 2, we designed a novel class of ET receptor antagonists based on a 1,3,4,5-tetrahydro-1H-benzo[e] [1,4]diazepin-2-one scaffold. Here, we report on the preparation as well as the in vitro and in vivo structure-activity relationships of these derivatives. Potent dual ETA/ETB receptor antagonists with affinities in the low nanomolar range have been identified. In addition, several compounds efficiently reduced arterial blood pressure after oral administration to Dahl salt sensitive rats. In this animal model, the efficacy of the benzo [e] [1,4] diazepin-2-one derivative rac-39au was superior to that of racemic ambrisentan, rac-2.

  DOI：

  10.1021/jm031115r
• 作为产物：
  描述：

  2,5-二甲基苯酚 、 氯乙酸 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 7.0h， 以82%的产率得到2,5-二甲基苯氧基乙酸
  参考文献：
  名称：

  苯并呋喃的有效合成及其在制备Calea属天然产物中的应用

  摘要：

  Lewis酸催化的β-取代烯烃2-芳氧基-3-二甲基氨基丙酸甲酯3a - 3f的分子内环化反应导致短而新颖的苯并呋喃2a - 2f的合成。当使用烯烃4-二甲基氨基-3-芳氧基-3-丁烯-2-酮4a – 4f时，环化过程更快，并提供了相应的取代的2-乙酰基苯并呋喃1a – 1f。在后者中，天然存在的化合物calebertin（1a），caleprunin A（1b）和caleprunin B（1c）以较高的总收率制备。这些苯并呋喃还可以通过在前驱体中用DMFDMA对前体1-芳氧基丙烷-2-酮7a - 7c进行MW辐射直接处理，然后添加催化剂而得到，从而使路线缩短了一个步骤。

  DOI：

  10.1016/j.tet.2005.08.015

文献信息

• Design, synthesis, and testing of potential antisickling agents. 4. Structure-activity relationships of benzyloxy and phenoxy acids
  作者：D. J. Abraham、P. E. Kennedy、A. S. Mehanna、D. C. Patwa、F. L. Williams

  DOI：10.1021/jm00374a006

  日期：1984.8

  small molecules, benzyloxy and phenoxy acids, as potent inhibitors of hemoglobin S (HbS) gelation. Structural modifications with a large number of each class confirm our earlier work that the highest activity is observed with compounds that contain dihalogenated aromatic rings with attached polar side chains. We have also found a halogenated aromatic malonic acid derivative to be quite active. Compounds

  在本文中，我们进一步确立了两类小分子，即苄氧基和苯氧基酸的活性，它们是血红蛋白S（HbS）凝胶化的有效抑制剂。每个类别都有大量结构修饰，这证实了我们较早的工作，即发现含有带有连接的极性侧链的二卤代芳环的化合物具有最高的活性。我们还发现卤代芳族丙二酸衍生物非常活泼。将本文报道的化合物与我们实验室研究的其他抗胶凝剂进行了比较。关于四种衍生物的抗胶凝活性和结合位点及其对血红蛋白（Hb）功能的变构机制的影响进行了评论。
• SUBSTITUTED BENZIMIDAZOLE DERIVATIVES
  申请人：Benson Gregory Martin

  公开号：US20090062356A1

  公开（公告）日：2009-03-05

  The invention is concerned with novel substituted benzimidazole derivatives of formula (I) wherein R 1 to R 10 and X are as defined in the description and in the claims, as well as physiologically acceptable salts and esters thereof. These compounds bind to FXR and can be used as medicaments.

  这项发明涉及式（I）的新型取代苯并咪唑衍生物，其中R1至R10和X如描述和权利要求中定义的那样，以及其生理上可接受的盐和酯。这些化合物与FXR结合，可用作药物。
• Gemfibrozil derivatives as activators of soluble guanylyl cyclase – A structure-activity study
  作者：Kevin M. Gayler、Jeremy M. Quintana、Jordan Mattke、Michael A. Plunk、Jessica H. Kostyo、Johann W. Karunananthan、Harold Nguyen、Mina Shuda、Liam D. Ferreira、Hannah Baker、Alexandra L. Stinchcomb、Iraida Sharina、Robert R. Kane、Emil Martin

  DOI：10.1016/j.ejmech.2021.113729

  日期：2021.11

  Previous studies demonstrated that anti-hyperlipidemic drug gemfibrozil acts as NO- and heme-independent activator of NO receptor soluble guanylyl cyclase. A series of new gemfibrozil derivatives were synthesized and evaluated for sGC activation. The structure-activity relationship study identified the positions in gemfibrozil's scaffold that are detrimental for sGC activation and those that are amendable

  先前的研究表明，抗高血脂药物吉非贝齐可作为 NO 受体可溶性鸟苷酸环化酶的 NO 和血红素非依赖性激活剂。合成了一系列新的吉非罗齐衍生物并评估了 sGC 的活化作用。构效关系研究确定了吉非罗齐支架中不利于 sGC 激活的位置以及可修正以优化修饰的位置。与吉非贝齐相比，化合物7c和15b是纯化 sGC 的 cGMP 形成活性的更有效激活剂，并且表现出预收缩的小鼠胸主动脉环的增强松弛。这些研究建立了进一步改进基于吉非贝齐支架的 sGC 激活剂所需的总体框架。
• Design, synthesis and anti-cancer evaluation of novel podophyllotoxin derivatives as potent tubulin-targeting agents
  作者：Cui Hu、Xiang Zhu、Gu-Hao Wang、Xun Wu、Hong-Wei Han、Gui-Hua Lu、Jin-Liang Qi、Yan-Jun Pang、Rong-Wu Yang、Xiao-Ming Wang、Yong-Hua Yang

  DOI：10.1007/s00044-017-1992-9

  日期：2018.2

  A series of podophyllotoxin derivatives (M1–M16) that were selectively acylated by various phenoxy acids at the C-4 position of podophyllotoxin were synthesized, and their biological activities were also evaluated. Among them, compound M4 showed the most potent anti-cancer activity against HeLa cells with an IC50 value of 1.64 ± 0.41 μM. Additionally, flow cytometry analysis results indicated that

  合成了一系列鬼臼毒素衍生物（M1 - M16），它们在鬼臼毒素的C-4位被各种苯氧基酸选择性地酰化，并对其生物学活性进行了评估。其中，化合物M4对HeLa细胞显示出最有效的抗癌活性，IC 50值为1.64±0.41μM。此外，流式细胞仪分析结果表明，它可能导致明显的细胞周期停滞在G2 / M期，但对细胞凋亡的诱导作用并不明显。此外，细胞周期相关蛋白CDK1的表达上调，而细胞周期蛋白B1和Cdc25C（有丝分裂起始所需的两种蛋白）的表达下调。此外，共聚焦测定和细胞外聚合微管蛋白表达分析还证明M4是有效的微管蛋白聚合抑制剂，其作用与秋水仙碱相当。最后，对接模拟结果表明，M4可以很好地结合微管蛋白的秋水仙碱结合位点，这进一步证实了M4对微管蛋白的抑制活性。
• Substituted 2-aminotetralins
  申请人：Discovery Therapeutics, Inc.

  公开号：US05430056A1

  公开（公告）日：1995-07-04

  Optically active or racemic compounds are provided having the formula ##STR1## where R.sub.1 is ##STR2## where Y is hydrogen, halogen or C.sub.1 to C.sub.6 linear or branched alkyl; R.sub.6 is C.sub.1 to C.sub.4 linear or branched alkyl; X is oxygen or sulfur; a is an integer from zero to 3; and n is an integer from 1 to 4. The compounds are capable of binding selectively to dopamine D.sub.2 receptors and are useful in treatment of disorders of the central nervous, cardiovascular and endocrine systems, such as intraocular pressure, schizophrenia and Parkinsonism, and for inducing anorexia and weight loss in humans and other mammals.

  提供具有以下公式的光学活性或外消旋化合物 ##STR1## 其中R.sub.1是 ##STR2## 其中Y是氢，卤素或C.sub.1到C.sub.6线性或支链烷基; R.sub.6是C.sub.1到C.sub.4线性或支链烷基; X是氧或硫; a是从零到3的整数; n是从1到4的整数。这些化合物能够选择性地结合到多巴胺D.sub.2受体，并且在治疗中枢神经，心血管和内分泌系统的疾病方面有用，例如眼内压，精神分裂症和帕金森病，并可在人类和其他哺乳动物中引起厌食和减重。

表征谱图