N-[4-(4-甲氧基苯甲酰基)苯基]乙酰胺 | 97732-63-3

• 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: N-[4-(4-甲氧基苯甲酰基)苯基]乙酰胺
• 英文名称: 4-(-acetylamino)-4'-methoxybenzophenone
• 英文别名: 4-acetylamino-4'-methoxybenzophenone；acetic acid-[4-(4-methoxy-benzoyl)-anilide]；Essigsaeure-[4-(4-methoxy-benzoyl)-anilid]；4'-Acetamino-4-methoxy-benzophenon；N-(4-{[4-(methyloxy)phenyl]carbonyl}phenyl)acetamide；Acetamide, N-[4-(4-methoxybenzoyl)phenyl]-；N-[4-(4-methoxybenzoyl)phenyl]acetamide
• CAS: 97732-63-3
• 化学式: C₁₆H₁₅NO₃
• 分子量: 269.3
• InChiKey: HEVLHYOMJRCYDO-UHFFFAOYSA-N

物化性质

• 熔点：
  172°C
• 沸点：
  500.8±35.0 °C(Predicted)
• 密度：
  1.198±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  N-[4-(4-甲氧基苯甲酰基)苯基]乙酰胺 在 盐酸 、 lithium aluminium tetrahydride 、 titanium(III) chloride 、 氢氟酸 、 sodium nitrite 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 6.5h， 生成 (Z)-1-(4-fluorophenyl)-1-(4-methoxyphenyl)-2-phenyl-1-butene
  参考文献：
  名称：

  Synthesis and receptor-binding affinity of fluorotamoxifen, a possible estrogen-receptor imaging agent

  摘要：

  Aminotamoxifen was totally synthesized from p-nitrobenzoyl chloride via a Friedel-Crafts acylation. Then, by means of a Balz-Schiemann reaction, aminotamoxifen was converted into fluorotamoxifen. The triazene variation of this conversion, with a 25% yield, enables a rapid, one-step diazotization, incorporating a fluorine atom into the phenyl ring of the tamoxifen. This reaction may be useful for the preparation of low specific activity 18F-labeled tamoxifen, for distribution, and for estrogen-receptor studies. For these in vivo and in vitro studies, fluorotamoxifen was also synthesized from p-fluorobenzoyl chloride, and its chemical intermediates were compared with estradiol and hexestrol, for their receptor binding and competition, as well as for their uterotropic activity. It is demonstrated that tamoxifen and fluorotamoxifen are strong estradiol agonists and partial hexestrol agonists, while aminotamoxifen is a weak estradiol and hexestrol agonist.

  DOI：

  10.1021/jm00148a022
• 作为产物：
  描述：

  4-甲氧基-4-硝基二苯甲酮 在 吡啶 、 sodium dithionite 作用下， 以 乙醇 为溶剂， 反应 0.08h， 生成 N-[4-(4-甲氧基苯甲酰基)苯基]乙酰胺
  参考文献：
  名称：

  Synthesis and receptor-binding affinity of fluorotamoxifen, a possible estrogen-receptor imaging agent

  摘要：

  Aminotamoxifen was totally synthesized from p-nitrobenzoyl chloride via a Friedel-Crafts acylation. Then, by means of a Balz-Schiemann reaction, aminotamoxifen was converted into fluorotamoxifen. The triazene variation of this conversion, with a 25% yield, enables a rapid, one-step diazotization, incorporating a fluorine atom into the phenyl ring of the tamoxifen. This reaction may be useful for the preparation of low specific activity 18F-labeled tamoxifen, for distribution, and for estrogen-receptor studies. For these in vivo and in vitro studies, fluorotamoxifen was also synthesized from p-fluorobenzoyl chloride, and its chemical intermediates were compared with estradiol and hexestrol, for their receptor binding and competition, as well as for their uterotropic activity. It is demonstrated that tamoxifen and fluorotamoxifen are strong estradiol agonists and partial hexestrol agonists, while aminotamoxifen is a weak estradiol and hexestrol agonist.

  DOI：

  10.1021/jm00148a022

文献信息

• Fluoro-clomiphene and its synthetic precursors: Synthesis and receptor binding
  作者：Aviv Gazit、Tania Livshitz、Shani Jashovam

  DOI：10.1016/0039-128x(86)90042-5

  日期：1986.7

  micrograms/rat/day for three days. In the receptor binding test both derivatives demonstrated similar displacement, with an A50% value in the 10(-5) M range, as compared to 10(-6) M for clomiphene and 10(-9) M for diethyl-stilbestrol. This synthesis may be useful for the preparation of 18F-labeled clomiphene for biodistribution studies.

  为了合成具有选择性雌激素受体结合的化合物，氟-和氨基-克罗米芬完全由苄基氯合成，并评估了它们的雌激素/抗雌激素活性以及它们的一些化学中间体的活性。由氨基-克罗米酚制备的三氮烯以39%的产率转化为氟-克罗米酚。在亲子宫试验中，氨基克罗米芬和氟克罗米芬均表现出中等强度的雌激素活性，最低饱和剂量为 50 和 100 微克/大鼠/天，持续三天。在受体结合测试中，这两种衍生物表现出类似的置换，A50% 值在 10(-5) M 范围内，而克罗米芬为 10(-6) M，二乙基己烯雌酚为 10(-9) M。
• Chemical Compounds
  申请人：Britton E. Jonathan

  公开号：US20070213348A1

  公开（公告）日：2007-09-13

  The present invention relates to novel compounds with a variety of therapeutic uses, more particularly novel substituted cyclic alkylidene compounds that are particularly useful for selective estrogen receptor modulation.

  本发明涉及一种具有各种治疗用途的新化合物，更特别地是新的取代环烷基烯化合物，这些化合物对于选择性雌激素受体调节非常有用。
• Cycloalkylidene Compounds As Modulators of Estrogen Receptor
  申请人：Fang Jing

  公开号：US20090253659A1

  公开（公告）日：2009-10-08

  The present invention relates to novel compounds with a variety of therapeutic uses, more particularly novel substituted cyclic alkylidene compounds that are particularly useful for selective estrogen receptor modulation.

  本发明涉及一种具有多种治疗用途的新化合物，更具体地说是新的取代环烷亚烯化合物，特别适用于选择性雌激素受体调节。
• Cycloalkylidene compounds as modulators of estrogen receptor
  申请人：Britton E. Jonathan

  公开号：US20070155839A1

  公开（公告）日：2007-07-05

  The present invention relates to novel compounds with a variety of therapeutic uses, more particularly novel substituted cyclic alkylidene compounds that are particularly useful for selective estrogen receptor modulation.

  本发明涉及一种具有多种治疗用途的新型化合物，更具体地说是一种新型的取代环烷亚烯化合物，对选择性雌激素受体调节特别有用。
• [EN] CYCLOALKYLIDENE COMPOUNDS AS MODULATORS OF ESTROGEN RECEPTOR<br/>[FR] COMPOSES CHIMIQUES
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2005012220A3

  公开（公告）日：2005-03-24