methyl-4-acetylamino-3-hydroxymethylbenzoate | 183430-66-2

• 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: methyl-4-acetylamino-3-hydroxymethylbenzoate
• 英文别名: methyl 4-acetamido-3-(hydroxymethyl)benzoate
• CAS: 183430-66-2
• 化学式: C₁₁H₁₃NO₄
• 分子量: 223.229
• InChiKey: BFLGTJWXBUSQFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl-4-acetylamino-3-hydroxymethylbenzoate 在 sodium hydroxide 作用下， 反应 8.0h， 以61%的产率得到4-Acetylamino-3-hydroxymethylbenzoic acid
  参考文献：
  名称：

  Design and Synthesis of Benzoic Acid Derivatives as Influenza Neuraminidase Inhibitors Using Structure-Based Drug Design

  摘要：

  A series of 94 benzoic acid derivatives was synthesized and tested for its ability to inhibit influenza neuraminidase. The enzyme-inhibitor complex structure was determined by X-ray crystallographic analysis for compounds which inhibited the enzyme. The most potent compound tested in vitro, 5 (4-(acetylamino)-3-guanidinobenzoic acid), had an IC50 = 2.5 x 10(-6) M against N9 neuraminidase. Compound 5 was oriented in the active site of the neuraminidase ina manner that was not predicted from the reported active site binding of GANA (4) with neuraminidase. In a mouse model of influenza, 5 did not protect the mice from weight loss due to the influenza virus when dosed intranasally.

  DOI：

  10.1021/jm970479e
• 作为产物：
  描述：

  methyl 4-acetamido-3-formylbenzoate 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.75h， 以73%的产率得到methyl-4-acetylamino-3-hydroxymethylbenzoate
  参考文献：
  名称：

  Design and Synthesis of Benzoic Acid Derivatives as Influenza Neuraminidase Inhibitors Using Structure-Based Drug Design

  摘要：

  A series of 94 benzoic acid derivatives was synthesized and tested for its ability to inhibit influenza neuraminidase. The enzyme-inhibitor complex structure was determined by X-ray crystallographic analysis for compounds which inhibited the enzyme. The most potent compound tested in vitro, 5 (4-(acetylamino)-3-guanidinobenzoic acid), had an IC50 = 2.5 x 10(-6) M against N9 neuraminidase. Compound 5 was oriented in the active site of the neuraminidase ina manner that was not predicted from the reported active site binding of GANA (4) with neuraminidase. In a mouse model of influenza, 5 did not protect the mice from weight loss due to the influenza virus when dosed intranasally.

  DOI：

  10.1021/jm970479e

文献信息

• Substituted benzene derivatives useful as neuraminidase inhibitors
  申请人：BioCryst Pharmaceuticals, Inc.

  公开号：US05602277A1

  公开（公告）日：1997-02-11

  A compound of the Formula (I): ##STR1## or pharmaceutically-suitable salts or prodrug forms thereof, wherein: n is 0-1; m is 0; p is 0-1; R.sup.1 is --CO.sub.2 H; R.sup.2 is selected from the group consisting of H, --OH, and --NH.sub.2 ; R.sup.3 is H; R.sup.4 is --C(O)NHR.sup.8 ; R.sup.5 is --NHC(R.sup.6)NH.sub.2 R.sup.6 is selected from the group consisting of .dbd.NH, .dbd.NOH, .dbd.NCN, .dbd.O, and .dbd.S; and R.sup.8 is selected from the group consisting of C.sub.1 -C.sub.4 linear or branched alkyl substituted with 0-3 halogens on each carbon.

  化合物的式子（I）：##STR1## 或其药物适用的盐或前药形式，其中：n为0-1；m为0；p为0-1；R.sup.1为--CO.sub.2 H；R.sup.2选自H、--OH和--NH.sub.2的群；R.sup.3为H；R.sup.4为--C（O）NHR.sup.8；R.sup.5为--NHC（R.sup.6）NH.sub.2；R.sup.6选自.dbd.NH、.dbd.NOH、.dbd.NCN、.dbd.O和.dbd.S的群；R.sup.8选自C.sub.1-C.sub.4线性或支链烷基，每个碳上取代0-3个卤素。
• US5602277A
  申请人：——

  公开号：US5602277A

  公开（公告）日：1997-02-11
• [EN] SUBSTITUTED BENZENE DERIVATIVES USEFUL AS NEURAMINIDASE INHIBITORS<br/>[FR] DERIVES DE BENZENE SUBSTITUES, UTILES COMME INHIBITEURS DE LA NEURAMINIDASE
  申请人：BIOCRYST PHARMACEUTICALS, INCORPORATED

  公开号：WO1996030329A1

  公开（公告）日：1996-10-03

  (EN) The invention relates to substituted benzenes and derivatives thereof, useful as neuraminidase inhibitors, to pharmaceutical compositions comprising such compounds, and to methods of using these compounds for treating viral and other infections.(FR) Benzènes substitués et dérivés desdits benzènes, utiles comme inhibiteurs de la neuraminidase, compositions pharmaceutiques renfermant de tels composés et méthodes d'utilisation de ces composés pour le traitement d'infections virales ou autres.
• Design and Synthesis of Benzoic Acid Derivatives as Influenza Neuraminidase Inhibitors Using Structure-Based Drug Design
  作者：Pooran Chand、Yarlagadda S. Babu、Shanta Bantia、Naiming Chu、L. Brent Cole、Pravin L. Kotian、W. Graeme Laver、John A. Montgomery、Ved P. Pathak、Sandra L. Petty、David P. Shrout、David A. Walsh、Gerald M. Walsh

  DOI：10.1021/jm970479e

  日期：1997.12.1

  A series of 94 benzoic acid derivatives was synthesized and tested for its ability to inhibit influenza neuraminidase. The enzyme-inhibitor complex structure was determined by X-ray crystallographic analysis for compounds which inhibited the enzyme. The most potent compound tested in vitro, 5 (4-(acetylamino)-3-guanidinobenzoic acid), had an IC50 = 2.5 x 10(-6) M against N9 neuraminidase. Compound 5 was oriented in the active site of the neuraminidase ina manner that was not predicted from the reported active site binding of GANA (4) with neuraminidase. In a mouse model of influenza, 5 did not protect the mice from weight loss due to the influenza virus when dosed intranasally.