3-Acetoxy-4-(acetylamino)-5-nitrobenzoic acid | 162252-44-0

• 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: 3-Acetoxy-4-(acetylamino)-5-nitrobenzoic acid
• 英文别名: 4-acetamido-3-acetyloxy-5-nitrobenzoic acid
• CAS: 162252-44-0
• 化学式: C₁₁H₁₀N₂O₇
• 分子量: 282.21
• InChiKey: GYXSFLQTJJYBDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  20
• 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：
  139
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-Acetoxy-4-(acetylamino)-5-nitrobenzoic acid 在 palladium on activated charcoal 肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以97%的产率得到3-Acetoxy-4-(acetylamino)-5-aminobenzoic acid
  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
• 作为产物：
  描述：

  4-氨基-3-羟基苯甲酸 在 盐酸 、 硝酸 、 sodium acetate 、 乙酸酐 作用下， 以 1,4-二氧六环 为溶剂， 生成 3-Acetoxy-4-(acetylamino)-5-nitrobenzoic acid
  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。
• 4-(Acetylamino)-3-hydroxy-5-nitrobenzoic Acid
  作者：M. J. Jedrzejas、M. Luo、S. Singh、W. J. Brouillette、G. M. Air

  DOI：10.1107/s0108270195003258

  日期：1995.9.15

  The 4-(acetylamino)-3-hydroxy-5-nitrobenzoic acid molecule, C9H8N2O6, a designed inhibitor for the influenza virus neuraminidase protein, crystallizes as hydrogen-bonded dimers. The dihedral angles of the substituent groups with respect to the planar phenyl moiety are 5.0(3)degrees for the carboxyl group, 45.0(2)degrees for the nitro group and 37.3(1)degrees for the acetylamino substituent. The crystal structure is stabilized by intermolecular hydrogen bonding.
• 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