3-乙酰氧基-4-(乙酰氨基)苯甲酸 | 162252-43-9

• 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-乙酰氧基-4-(乙酰氨基)苯甲酸
• 英文名称: 3-Acetoxy-4-(acetylamino)benzoic acid
• 英文别名: 4-(acetylamino)-3-acetoxybenzoic acid；4-acetamido-3-acetyloxybenzoic acid
• CAS: 162252-43-9
• 化学式: C₁₁H₁₁NO₅
• 分子量: 237.212
• InChiKey: ZNHZOYIHGBRZNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  92.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-乙酰氧基-4-(乙酰氨基)苯甲酸 在 sodium hydroxide 作用下， 反应 0.5h， 以49%的产率得到4-(乙酰基氨基)-3-羟基苯甲酸
  参考文献：
  名称：

  基于结构的流感病毒唾液酸酶抑制剂。具有新颖相互作用的苯甲酸铅。

  摘要：

  流感病毒唾液酸酶是一种表面酶，对于感染病毒至关重要。在所有已知的流感变体中，催化位点均高度保守，表明该蛋白是药物干预的合适靶标。最有效的已知抑制剂是2-脱氧-2，3-二氢-N-乙酰神经氨酸（Neu5Ac2en），特别是4-胍基衍生物（4-胍基-Neu5Ac2en）的类似物。我们利用4-（N-乙酰氨基）苯甲酸的苯环作为环状模板替代Neu5Ac2en的二氢吡喃环。在这项研究中，准备了几种3-（N-酰基氨基）衍生物作为Neu5Ac2en甘油侧链的潜在替代物，并且发现其中一些与唾液酸酶的相同结合亚位相互作用。更重要的意义是观察到，迄今为止确定的最有效的流感唾液酸酶苯甲酸抑制剂（IC50 = 10 microM）3-胍基苯甲酸衍生物（相当于4-胍基-Neu5Ac2en的4-胍基）。与胍基结合子位点相反，唾液酸酶上的甘油结合子位点。因此，该苯甲酸衍生物提供了一种新化合物，该化合物以新颖的方式与流感唾液酸酶的催化​​位点相互作用。

  DOI：

  10.1021/jm00017a005
• 作为产物：
  描述：

  乙酸酐 、 4-氨基-3-羟基苯甲酸 在 盐酸 、 sodium acetate 作用下， 以58%的产率得到3-乙酰氧基-4-(乙酰氨基)苯甲酸
  参考文献：
  名称：

  Aromatic sialic acid analogues as potential inhibitors of influenza virus neuraminidase

  摘要：

  The influenza virus neuraminidase (NA) is an enzyme essential for viral infection and offers a potential target for antiviral drug development. We aimed our research at the synthesis of non-carbohydrate molecules able to inhibit NA as transition-state analogues. Aromatic sialic acid analogues (compound 5 and compound 10) were synthesised in good yields starting from commercially available benzoic acids using a suitable synthetic strategy. (C) 2001 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(01)01081-3

文献信息

• Inhibitors of influenza virus neuraminidase and methods of making and
  申请人：The University of Alabama at Birmingham

  公开号：US05453533A1

  公开（公告）日：1995-09-26

  An influenza virus neuraminidase inhibitor, its analogs, its pharmaceutically acceptable salts, derivatives, and mixtures thereof having the following formula: ##STR1## where A is CO.sub.2 H, CO.sub.2 H.sub.3, NO.sub.2, SO.sub.3 H or PO.sub.3 H.sub.2, B is CH, N, O or S, R.sub.1 and R.sub.2 are H, NO.sub.2 or (CH.sub.m).sub.n X.sub.1 where m=1 or 2, n is an integer from 0 to 4 and X.sub.1 is guanidino, OH, NH.sub.2, SH, NO.sub.2, F, Cl, Br, I, CN, CF.sub.3, CO.sub.2 H, SO.sub.3 H or PO.sub.3 H.sub.2, R.sub.3 and R.sub.4 are H, (CH.sub.o).sub.p X.sub.2, (CH.sub.o).sub.p CHX.sub.2 CH.sub.2 X.sub.2, NH(CH.sub.o).sub.p CHX.sub.2 CH.sub.2 X.sub.2, NHCO(CH.sub.o).sub.p CH.sub.2 X.sub.2 or NHCO(CH.sub.o).sub.p CHX.sub.2 CH.sub.2 X.sub.2 where o=1 or 2, p is an integer from 0 to 4 and X.sub.2 is H, guanidino, OH, NH.sub.2, SH, NO.sub.2, CF.sub.3, CO.sub.2 H, SO.sub.3 H or PO.sub.3 H.sub.2 , R.sub.5 =H, OH, NH.sub.2, (CH.sub.k).sub.1 X.sub.3, CO(CH.sub.k).sub.1 X.sub.3, SO(CH.sub.k).sub.1 X.sub.3 or SO.sub.2 (CH.sub.k).sub.1 X.sub.3 where k=1 or 2, 1 is an integer from 0 to 4 and X.sub.3 is guanidino, OH, NH.sub.2, SH, NO.sub.2, CF.sub.3, CO.sub.2 H, SO.sub.3 H or PO.sub.3 H.sub.2, R.sub.6 is H, CH(OH)X.sub.4, CH(NH.sub.2)X.sub.4, COX.sub.4, SOX.sub.4, or SO.sub.2 X.sub.4, where X.sub.4 is H, CH.sub.3, CH.sub.3 CH.sub.2, CH.sub.3 CHCH.sub.3, CH.sub.3 CH.sub.2 CH.sub.2 or halogen substituted analogs of X.sub.4. The inhibitor in a composition with a pharmaceutically acceptable carrier. A method of inhibiting influenza virus neuraminidase where the inhibitor is administered to a subject in a pharmaceutically acceptable amount along with effective amounts of a pharmaceutically acceptable carrier. Methods of marking a pharmaceutical composition of an acceptable carrier and the inhibitor. Methods of treating and preventing a subject infected with influenza virus (type A or B) using the inhibitor.

  一种流感病毒神经氨酸酶抑制剂，其类似物，其药用可接受的盐，衍生物和混合物具有以下结构式：##STR1##其中A为CO.sub.2 H，CO.sub.2 H.sub.3，NO.sub.2，SO.sub.3 H或PO.sub.3 H.sub.2，B为CH，N，O或S，R.sub.1和R.sub.2为H，NO.sub.2或(CH.sub.m).sub.n X.sub.1，其中m=1或2，n是0到4的整数，X.sub.1为胍基，OH，NH.sub.2，SH，NO.sub.2，F，Cl，Br，I，CN，CF.sub.3，CO.sub.2 H，SO.sub.3 H或PO.sub.3 H.sub.2，R.sub.3和R.sub.4为H，(CH.sub.o).sub.p X.sub.2，(CH.sub.o).sub.p CHX.sub.2 CH.sub.2 X.sub.2，NH(CH.sub.o).sub.p CHX.sub.2 CH.sub.2 X.sub.2，NHCO(CH.sub.o).sub.p CH.sub.2 X.sub.2或NHCO(CH.sub.o).sub.p CHX.sub.2 CH.sub.2 X.sub.2，其中o=1或2，p是0到4的整数，X.sub.2为H，胍基，OH，NH.sub.2，SH，NO.sub.2，CF.sub.3，CO.sub.2 H，SO.sub.3 H或PO.sub.3 H.sub.2，R.sub.5=H，OH，NH.sub.2，(CH.sub.k).sub.1 X.sub.3，CO(CH.sub.k).sub.1 X.sub.3，SO(CH.sub.k).sub.1 X.sub.3或SO.sub.2(CH.sub.k).sub.1 X.sub.3，其中k=1或2，l是0到4的整数，X.sub.3为胍基，OH，NH.sub.2，SH，NO.sub.2，CF.sub.3，CO.sub.2 H，SO.sub.3 H或PO.sub.3 H.sub.2，R.sub.6为H，CH(OH)X.sub.4，CH(NH.sub.2)X.sub.4，COX.sub.4，SOX.sub.4或SO.sub.2 X.sub.4，其中X.sub.4为H，CH.sub.3，CH.sub.3 CH.sub.2，CH.sub.3 CHCH.sub.3，CH.sub.3 CH.sub.2 CH.sub.2或X.sub.4的卤素取代物。抑制剂与药用可接受的载体组成的组合物。一种抑制流感病毒神经氨酸酶的方法，其中将抑制剂与药用可接受的载体一起以药用可接受的剂量给予受试者。标记含有可接受载体和抑制剂的药物组合物的方法。使用该抑制剂治疗和预防感染流感病毒（A型或B型）的受试者的方法。
• Methods of inhibiting bacterial sialidase
  申请人：The University of Alabama

  公开号：US05985859A1

  公开（公告）日：1999-11-16

  A method of inhibiting bacterial sialidase comprising administering to a subject an inhibiting effective amount of a compound of formula I: ##STR1## wherein A is CO.sub.2 H, PO.sub.2 H, or SO.sub.2 H; B is N; R.sub.1 and R.sub.2 are H; R.sub.3 and R.sub.4 are, independently, H, OH, NO.sub.2, guanidino, or alkyl or alkenyl of from 1 to 3 carbons where the alkyl or alkenyl is unsubstituted or is substituted, independently, with one or more of OH, NH2, or halide; R.sub.5 is H; and R.sub.6 is COCH.sub.3, or COCI.sub.3 ; or an analog, pharmaceutically acceptable salt, derivative, or mixture thereof. A method of preventing a bacterial or trypanosomal infection using the compounds of formula I. A method of treating a bacterial or trypanosomal infection using the compounds of formula I. A pharmaceutical composition comprising a pharmaceutically acceptable carrier admixed with an inhibiting effective amount of a compound of formula I. A method of making a pharmaceutical composition, comprising admixing a pharmaceutically acceptable carrier with an inhibiting effective amount of a compound of formula I.

  一种抑制细菌唾液酸酶的方法，包括向受试者施用化合物I的抑制有效量：其中A为CO₂H、PO₂H或SO₂H；B为N；R₁和R₂为H；R₃和R₄独立地为H、OH、NO₂、胍基或1至3个碳原子的烷基或烯基，其中烷基或烯基未取代或独立地取代为一个或多个OH、NH₂或卤素；R₅为H；R₆为COCH₃或COCI₃；或其类似物、药学上可接受的盐、衍生物或其混合物。使用化合物I预防细菌或锥虫感染的方法。使用化合物I治疗细菌或锥虫感染的方法。包括与化合物I的抑制有效量混合的药学上可接受的载体的制药组合物。制备制药组合物的方法，包括将药学上可接受的载体与化合物I的抑制有效量混合。
• INHIBITORS OF INFLUENZA VIRUS NEURAMINIDASE AND METHODS OF MAKING AND USING THE SAME
  申请人：THE UNIVERSITY OF ALABAMA AT BIRMINGHAM

  公开号：EP0755372A1

  公开（公告）日：1997-01-29
• EP0755372A4
  申请人：——

  公开号：EP0755372A4

  公开（公告）日：1997-09-10
• US5453533A
  申请人：——

  公开号：US5453533A

  公开（公告）日：1995-09-26