3-Nitro-4-acetamidobenzyl alcohol | 73166-06-0

• 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-Nitro-4-acetamidobenzyl alcohol
• 英文别名: 4-(hydroxymethyl)-2-nitroacetanilide；N-[4-(hydroxymethyl)-2-nitrophenyl]acetamide
• CAS: 73166-06-0
• 化学式: C₉H₁₀N₂O₄
• 分子量: 210.189
• InChiKey: XAXCFFLLLSKDBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  95.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-Nitro-4-acetamidobenzyl alcohol 在 镍 sodium hydroxide 、 氢气 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、245.15 kPa 条件下， 反应 1.0h， 生成 (3,4-二氨基苯基)甲醇
  参考文献：
  名称：

  Akhtar, M. Shamim; Seth, M.; Bhaduri, A. P., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 395 - 399

  摘要：

  DOI：
• 作为产物：
  描述：

  对乙酰氨基苯甲酸 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 硝酸 作用下， 以 四氢呋喃 、 乙醚 、 氯仿 、 水 为溶剂， 反应 24.0h， 生成 3-Nitro-4-acetamidobenzyl alcohol
  参考文献：
  名称：

  Structure-Activity Relationship of Omeprazole and Analogs as Helicobacter pylori Urease Inhibitors

  摘要：

  Helicobacter pylori urease belongs to a family of highly conserved urea-hydrolyzing enzymes. A common feature of these enzymes is the presence of two Lewis acid nickel ions and a reactive cysteine residue in the active site. The H+/K(+)-ATPase inhibitor omeprazole is a prodrug of a sulfenamide which covalently modifies cysteine residues on the luminal side of the H+/K(+)-ATPase of gastric parietal cells. Omeprazole and eight analogues were selected based on their chemical, electronic, and kinetic properties, and each was incubated with viable H. pylori in phosphate-buffered saline at pH 7.4 for 30 min, after which 100 mM urea was added and the amount of ammonia formed analyzed after a further 10 min. Inhibition between 0% and 100% at a 0.1 mM concentration was observed for the different analogues and could be expressed as a function of the pKa-value of the pyridine, the pKa-value of the benzimidazole, the overall lipophilicity, and, most importantly, the rate of sulfenamide formation, in a quantitative structure-activity relationship. The inhibition was potentiated by a lower pH (favoring the formation of the sulfenamide) but abolished in the presence of beta-mercaptoethanol (a scavenger of the sulfenamide). Structural analogues incapable of yielding the sulfenamide did not inhibit ammonia production. Treatment of Helicobacter felis-infected mice with 230 mumol/kg flurofamide b.i.d. for 4 weeks, known to potently inhibit urease activity in vivo, as a means of eradicating the infection, was tested and compared with the effect of 125 mumol/kg omeprazole b.i.d. for 4 weeks. Neither treatment proved efficacious.

  DOI：

  10.1021/jm00025a008

文献信息

• Substituted thio-, sulfinyl-, and sulfonyl-alkyl benzimidazole carbamates
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04154846A1

  公开（公告）日：1979-05-15

  Benzimidazole carbamate derivatives are provided having the structure ##STR1## wherein R is lower alkyl, lower alkenylalkyl, lower alkynylalkyl, phenyl, substituted phenyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkenylalkyl or phenylalkyl, R.sup.1 is lower alkyl, phenylalkyl or di-lower alkylaminoalkyl, Z is a single bond or a straight or branched chain alkylene group, and n is 0, 1 or 2. These compounds are useful as anthelmintic agents administered orally or parenterally.

  提供了具有结构##STR1##的苯并咪唑羰基衍生物，其中R是较低的烷基、较低的烯烃基烷基、较低的炔烃基烷基、苯基、取代苯基、环烷基、环烯烃基、环烷基烷基、环烯烃基烷基或苯基烷基，R.sup.1是较低的烷基、苯基烷基或二较低烷基氨基烷基，Z是单键或直链或支链烷基基团，n为0、1或2。这些化合物可作为口服或静脉注射的驱虫剂。
• New benzimidazoles as thrombopoietin receptor agonists
  作者：Igor G. Safonov、Dirk A. Heerding、Richard M. Keenan、Alan T. Price、Connie L. Erickson-Miller、Christopher B. Hopson、Jenna L. Levin、Kenneth A. Lord、Peter M. Tapley

  DOI：10.1016/j.bmcl.2005.11.096

  日期：2006.3

  A novel benzimidazole series of small-molecule thrombopoietin receptor agonists has been discovered. Herein, we discuss the preliminary exploration of structure-activity relationships within this chemotype. (C) 2005 Elsevier Ltd. All rights reserved.
• SCHMIDHAMMER, H.;HOHENIOHE-OEHRINGEN, K., SCI. PHARM., 1983, 51, N 1, 8-16
  作者：SCHMIDHAMMER, H.、HOHENIOHE-OEHRINGEN, K.

  DOI：——

  日期：——
• AKHTAR M. SHAMIM; SETH M.; BHADURI A. P., INDIAN J. CHEM., 25,(1986) N 4, 395-399
  作者：AKHTAR M. SHAMIM、 SETH M.、 BHADURI A. P.

  DOI：——

  日期：——
• US4154846A
  申请人：——

  公开号：US4154846A

  公开（公告）日：1979-05-15