3-乙酰氨基苯甲酸乙酯 | 19305-32-9

• 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: 3-乙酰氨基苯甲酸乙酯
• 英文名称: 3-acetylaminobenzoic acid ethyl ester
• 英文别名: 3-acetylamino-benzoic acid ethyl ester；3-Acetylamino-benzoesaeure-aethylester；3-Acetamino-benzoesaeure-aethylester；m-(N-Acetylamino)-benzoesaeureaethylester；m-Ethylacetamidobenzoat；Ethyl 3-acetamidobenzoate
• CAS: 19305-32-9
• 化学式: C₁₁H₁₃NO₃
• mdl: MFCD01161890
• 分子量: 207.229
• InChiKey: LVOGEXYCOVAAIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-乙酰氨基苯甲酸乙酯 在 copper(l) iodide 、 铜 、 potassium carbonate 作用下， 以 甲醇 、 二丁醚 为溶剂， 反应 97.5h， 生成 methyl 3-(4-methoxycarbonylphenylamino)benzoate
  参考文献：
  名称：

  A Novel Class of Potent Nonglycosidic and Nonpeptidic Pan-Selectin Inhibitors

  摘要：

  An early step of the inflammatory response, the rolling of leukocytes on activated endothelial cells, is mediated by selectin/carbohydrate interactions. The tetrasaccharide sialy Lewis(x) is a ligand for E-, P-, and L-selectin and therefore serves as a lead structure for the development of analogues. A combination of synthesis and structure-based design allowed rapid optimization. The current lead 2a was evaluated in our E-selectin cell flow chamber assay where it proved to inhibit rolling and adhesion with an IC50 of 28 +/- 7 mu M. The assays used are predictive for the in vivo efficacy of test compounds as shown for 2a in a proteose peptone induced peritonitis model of acute inflammation in mice.

  DOI：

  10.1021/jm060468y
• 作为产物：
  描述：

  3-氨基苯甲酸乙酯 生成 3-乙酰氨基苯甲酸乙酯
  参考文献：
  名称：

  76.氢原子的缔合作用。第二部分取代的苯胺类及相关物质

  摘要：

  DOI：

  10.1039/jr9380000375

文献信息

• Simple, convenient, and direct conversion of anilines and anilides into arynes
  作者：B. Baigrie、J. I. G. Cadogan、J. R. Mitchell、A. K. Robertson、J. T. Sharp

  DOI：10.1039/p19720002563

  日期：——

  Reaction of aniline with pentyl nitrite and acetic anhydride in benzene, or other solvents, gives benzyne in up to 32% yield as measured by trapping with anthracene, and tetraphenylcyclopentadienone and its 2,5-di-p-tolyl analogue. The role of the anhydride is to by-pass the suppressive effect of water on benzyne formation from the diazonium acetate ion pair. Reaction in benzene of aniline–acetic anhydride

  苯胺与亚硝酸戊酯和乙酸酐在苯或其他溶剂中的反应，通过捕获蒽，四苯基环戊二烯酮及其2,5-二-对甲苯基类似物，测得苯并炔的收率高达32％。酸酐的作用是绕过水对乙酸重氮盐离子对生成苯并炔的抑制作用。苯胺-乙酸酐或（较好的）乙酰苯胺在苯中与亚硝酸对氯苯甲酰酯（PCBN）反应（通过对氯苯甲酸银和亚硝酰氯的反应）可得到高达71％的苯并苯，通过之前和9的捕集测得，10，2-二甲氧基蒽，并通过与甲基丙烯酸甲酯的烯反应，得到2-亚甲基-3-苯基丙酸乙酯（31％）。元取代的苯胺和乙酰苯胺（米-XC 6 ħ 4 ·-NHAc; X = F，氯，溴，I，CO 2的Et，的MeO，卜吨，CF 3，或NO 2）和3-氨基吡啶的行为像苯胺和除了邻氨基苯甲酸乙酯，2,5-二甲氧基和2,5-二氯苯胺以外，对乙酰苯胺的对位异构体的收率较低，邻位异构体的芳烃很少或没有。
• Introduction of a Hydroxy Group at the Para Position and <i>N</i>-Iodophenylation of <i>N</i>-Arylamides Using Phenyliodine(III) Bis(Trifluoroacetate)
  作者：Naoki Itoh、Takeshi Sakamoto、Etsuko Miyazawa、Yasuo Kikugawa

  DOI：10.1021/jo0260847

  日期：2002.10.1

  The reaction of anilides with phenyliodine(III) bis(trifluoroacetate) (PIFA) in trifluoroacetic acid (TFA), TFA-CHCl3, or hexafluoroisopropyl alcohol (HFIP) is described. When the acyl group of the anilide is highly electronegative, such as trifluoroacetyl, or the phenyl group is substituted with an electron-withdrawing group, the 4-iodophenyl group is transferred from PIFA to the amide nitrogen to

  描述了在三氟乙酸（TFA），TFA-CHCl3或六氟异丙醇（HFIP）中，苯甲酸酯与苯基碘（III）双（三氟乙酸酯）（PIFA）的反应。当苯胺的酰基具有高负电性时，例如三氟乙酰基，或者苯基被吸电子基团取代，则4-碘苯基从PIFA转移到酰胺氮上，得到乙酰基二芳基胺。另一方面，当酰基具有诸如4-甲氧基苯基之类的供电子功能时，或者苯基被供电子性基团取代时，三氟乙酰氧基被转移至苯胺芳环的对位。该组在后处理过程中水解产生相应的苯酚。
• Tricyclic compounds in treating hyperalgesic conditions and NIDDM
  申请人：Novo Nordisk A/S

  公开号：US05962449A1

  公开（公告）日：1999-10-05

  The present invention relates to novel N-substituted amino acids and esters thereof in which a substituted alkyl chain forms part of the N-substituent or salts thereof, to methods for their preparation, to compositions containing them, and to their use for the clinical treatment of painful, hyperalgesic and/or inflammatory conditions in which C-fibers play a pathophysiological role by eliciting neurogenic pain or inflammation.

  本发明涉及新颖的N-取代氨基酸及其酯，其中取代的烷基链形成N-取代基的一部分或其盐，以及它们的制备方法、含有它们的组合物，以及它们在临床治疗疼痛、过敏性疼痛和/或炎症情况中的用途，其中C-纤维通过引发神经源性疼痛或炎症发挥病理生理作用。
• Discovery and synthesis of 1,2,4-oxadiazole derivatives as novel inhibitors of Zika, dengue, Japanese encephalitis, and classical swine fever virus infections
  作者：Sangwoo Nam、Hyo Gyeong Na、Eun Hye Oh、Eunhye Jung、Yeon Hee Lee、Eun Ju Jeong、Yu-Da Ou、Bin Zhou、Sunjoo Ahn、Jin Soo Shin、Soo Bong Han、Yun Young Go

  DOI：10.1007/s12272-022-01380-8

  日期：2022.4

  Zika virus (ZIKV), an arbovirus of the Flaviviridae family, has emerged as a significant public health concern owing to its association with congenital abnormalities and severe neurological sequelae. Thus, there is an urgent need to develop effective therapeutic approaches to efficiently treat ZIKV infections. This study used phenotypic screening to identify a series of 1,2,4-oxadiazole derivatives that possess antiviral activity against ZIKV infection. Subsequently, 28 new derivatives were designed, synthesized, and evaluated for this purpose. Among these compounds, 4-(5-phenyl-1,2,4-oxadiazol-3-yl)-N-(pyridin-3-ylmethyl)aniline (5d) had potent antiviral activity against ZIKV infections. Furthermore, a structure–activity relationship analysis indicated that a benzyl substitution on the aniline nitrogen of this compound improved potency while augmenting its drug-like properties. In addition, 5d exhibited antiviral activity against various viruses of Flaviviridae family of worldwide public health importance, such as dengue, Japanese encephalitis and classical swine fever viruses, indicating its potential as a lead compound for generating 1,2,4-oxadiazole derivatives with broad-spectrum anti-flaviviral properties.

  寨卡病毒（ZIKV）是黄病毒科的一种虫媒病毒，由于与先天性畸形和严重的神经系统后遗症有关，已成为一个重大的公共卫生问题。因此，迫切需要开发有效的治疗方法来有效治疗 ZIKV 感染。本研究利用表型筛选鉴定了一系列具有抗 ZIKV 感染病毒活性的 1,2,4-恶二唑衍生物。随后，为此目的设计、合成和评估了28种新的衍生物。在这些化合物中，4-(5-苯基-1,2,4-恶二唑-3-基)-N-(吡啶-3-基甲基)苯胺(5d)对寨卡病毒感染具有有效的抗病毒活性。此外，结构-活性关系分析表明，该化合物苯胺氮上的苄基取代提高了效力，同时增强了其药物样特性。此外，5d 对对全球公共卫生具有重要意义的黄病毒科多种病毒（例如登革热、日本脑炎和猪瘟病毒）表现出抗病毒活性，表明其作为先导化合物用于生成具有广泛作用的 1,2,4-恶二唑衍生物的潜力。 -广谱抗黄病毒特性。
• Enantioselective palladium(0)-catalyzed intramolecular cyclopropane functionalization: access to dihydroquinolones, dihydroisoquinolones and the BMS-791325 ring system
  作者：J. Pedroni、T. Saget、P. A. Donets、N. Cramer

  DOI：10.1039/c5sc01909e

  日期：——

  Taddol-based phosphoramidite ligands enable enantioselective palladium(0)-catalyzed C-H arylation of cyclopropanes. The cyclized products are obtained in high yields and enantioselectivities. The reported method provides an efficient access to a broad...

  Taddol基于亚磷酰胺配体使环丙烷的对映选择性钯（0）催化CH芳基化。以高收率和对映选择性获得环化产物。报告的方法可有效访问广泛的...