ethyl 2-(4-((tert-butoxycarbonyl)amino)phenyl)acetate | 897648-31-6

• 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: ethyl 2-(4-((tert-butoxycarbonyl)amino)phenyl)acetate
• 英文别名: Ethyl 2-(4-((tert-butoxycarbonyl)amino)phenyl)acetate；ethyl 2-[4-[(2-methylpropan-2-yl)oxycarbonylamino]phenyl]acetate
• CAS: 897648-31-6
• 化学式: C₁₅H₂₁NO₄
• mdl: MFCD11458703
• 分子量: 279.336
• InChiKey: OWSWVIDBJRARAZ-UHFFFAOYSA-N

物化性质

• 沸点：
  339.7±25.0 °C(Predicted)
• 密度：
  1.127±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.466
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-(4-((tert-butoxycarbonyl)amino)phenyl)acetate 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 以99%的产率得到tert-butyl N-[4-(2-oxoethyl)phenyl]carbamate
  参考文献：
  名称：

  A Structure–Activity Analysis of Biased Agonism at the Dopamine D2 Receptor

  摘要：

  Biased agonism offers an opportunity for the medicinal chemist to discover pathway-selective ligands for GPCRs. A number of studies have suggested that biased agonism at the dopamine D2 receptor (D2R) may be advantageous for the treatment of neuropsychiatric disorders, including schizophrenia. As such, it is of great importance to gain insight into the SAR of biased agonism at this receptor. We have generated SAR based on a novel D2R partial agonist, tert-butyl (trans-4-(2-(3,4dihydroisoquinolin-2(1H)-yOethyl)cyclohexyl)carbamate (4). This ligand shares structural similarity to cariprazine (2), a drug awaiting FDA approval for the treatment of schizophrenia, yet displays a distinct bias toward two different signaling end points. We synthesized a number of derivatives of 4 with subtle structural modifications, including incorporation of cariprazine fragments. By combining pharmacological profiling with analytical methodology to identify and to quantify bias, we have demonstrated that efficacy and biased agonism can be finely tuned by minor structural modifications to the head group containing the tertiary amine, a tail group that extends away from this moiety, and the orientation and length of a spacer region between these two moieties.

  DOI：

  10.1021/jm401318w
• 作为产物：
  描述：

  对硝基苯乙酸乙酯 在 盐酸 、 tin 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 ethyl 2-(4-((tert-butoxycarbonyl)amino)phenyl)acetate
  参考文献：
  名称：

  A Structure–Activity Analysis of Biased Agonism at the Dopamine D2 Receptor

  摘要：

  Biased agonism offers an opportunity for the medicinal chemist to discover pathway-selective ligands for GPCRs. A number of studies have suggested that biased agonism at the dopamine D2 receptor (D2R) may be advantageous for the treatment of neuropsychiatric disorders, including schizophrenia. As such, it is of great importance to gain insight into the SAR of biased agonism at this receptor. We have generated SAR based on a novel D2R partial agonist, tert-butyl (trans-4-(2-(3,4dihydroisoquinolin-2(1H)-yOethyl)cyclohexyl)carbamate (4). This ligand shares structural similarity to cariprazine (2), a drug awaiting FDA approval for the treatment of schizophrenia, yet displays a distinct bias toward two different signaling end points. We synthesized a number of derivatives of 4 with subtle structural modifications, including incorporation of cariprazine fragments. By combining pharmacological profiling with analytical methodology to identify and to quantify bias, we have demonstrated that efficacy and biased agonism can be finely tuned by minor structural modifications to the head group containing the tertiary amine, a tail group that extends away from this moiety, and the orientation and length of a spacer region between these two moieties.

  DOI：

  10.1021/jm401318w

文献信息

• Modular Synthesis of Arylacetic Acid Esters, Thioesters, and Amides from Aryl Ethers via Rh(II)-Catalyzed Diazo Arylation
  作者：Daniel Best、Mickaël Jean、Pierre van de Weghe

  DOI：10.1021/acs.joc.6b01426

  日期：2016.9.2

  One-pot formation of arylacetic acid esters, thioesters, and amides via Rh(II)-catalyzed arylation of a Meldrum’s acid-derived diazo reagent with electron-rich arenes is described. The methodology was used to efficiently synthesize an anticancer compound.

  描述了通过Rh（II）催化的Meldrum酸衍生的重氮试剂与富电子芳烃的一锅法形成的芳基酸酯，硫酯和酰胺。该方法用于有效合成抗癌化合物。
• [EN] COMPOUNDS AND THEIR METHODS OF USE<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES ET LEURS PROCÉDÉS D'UTILISATION
  申请人：AGIOS PHARMACEUTICALS INC

  公开号：WO2014079150A1

  公开（公告）日：2014-05-30

  Provided are compounds of formula (I), which can inhibit glutaminase. Pharmaceutical compositions comprising these compounds and uses as glutaminase inhibitors for treating cancers thereof are also provided.

  提供了化合物的化学式(I)，可以抑制谷氨酸酶。还提供了包含这些化合物的药物组合物，并用作抑制谷氨酸酶以治疗相关癌症的用途。
• Efficient cyclopropanation of aryl/heteroaryl acetates and acetonitriles with vinyl diphenyl sulfonium triflate
  作者：Mingwei Zhou、Yimin Hu、Ke En、Xuefei Tan、Hong C. Shen、Xuhong Qian

  DOI：10.1016/j.tetlet.2018.02.080

  日期：2018.4

  A convenient method was developed for the cyclopropanation of aryl acetates and aryl acetonitrile using vinyl diphenyl sulfonium triflate salt. The newly developed conditions are simple, mild, and compatible with a wide range of functional groups, without the need to apply an inert atmosphere, or alkali bases.

  开发了一种方便的方法，该方法使用乙烯基二苯基sulf三氟甲磺酸盐对乙酸芳基酯和芳基乙腈进行环丙烷化。新开发的条件简单，温和，并且与各种官能团兼容，而无需施加惰性气氛或碱金属。
• [EN] COMPOUNDS, PHARMACEUTICAL COMPOSITIONS AND USES AS GLUTAMINASE INHIBITORS FOR TREATING CANCERS THEREOF<br/>[FR] COMPOSÉS, COMPOSITIONS PHARMACEUTIQUES ET UTILISATIONS DES COMPOSÉS EN TANT QU'INHIBITEURS DE GLUTAMINASE POUR LE TRAITEMENT DE CANCERS ASSOCIÉS
  申请人：AGIOS PHARMACEUTICALS INC

  公开号：WO2014079136A1

  公开（公告）日：2014-05-30

  Provided are compounds of formula (I), wherein X, Y, Z, W, m, n, o, p, R1, R2 and R6 are defined as in the description. Pharmaceutical compositions and uses as glutaminase inhibitors for treating cancers thereof are also provided.

  提供了化合物的结构式（I），其中X、Y、Z、W、m、n、o、p、R1、R2和R6的定义如描述中所述。还提供了作为谷氨酰胺酶抑制剂用于治疗癌症的药物组合物和用途。
• COMPOUNDS AND THEIR METHODS OF USE
  申请人：Lemieux Rene M.

  公开号：US20140142081A1

  公开（公告）日：2014-05-22

  Compounds and compositions comprising compounds that inhibit glutaminase are described herein. Also described herein are methods of using the compounds that inhibit glutaminase in the treatment of cancer.

  本文描述了含有抑制谷氨酸酶的化合物和组合物。本文还描述了利用这些抑制谷氨酸酶的化合物治疗癌症的方法。