diethyl (4-benzyloxy)phenylacetyl phosphonate | 84891-45-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: diethyl (4-benzyloxy)phenylacetyl phosphonate
• 英文别名: 1-Diethoxyphosphoryl-2-(4-phenylmethoxyphenyl)ethanone
• CAS: 84891-45-2
• 化学式: C₁₉H₂₃O₅P
• 分子量: 362.362
• InChiKey: LZLIMCKZYAOAKJ-UHFFFAOYSA-N

物化性质

• 沸点：
  480.9±47.0 °C(Predicted)
• 密度：
  1.180±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl (4-benzyloxy)phenylacetyl phosphonate 在 nickel dichloride sodium tetrahydroborate 、 盐酸羟胺 作用下， 以 吡啶 、 甲醇 、 正己烷 为溶剂， 反应 88.0h， 生成
  参考文献：
  名称：

  [EN] NOVEL PHOSPHORUS-CONTAINING THYROMIMETICS
  [FR] NOUVELLES SUBSTANCES THYROMIMETIQUES CONTENANT DU PHOSPHORE

  摘要：

  公开号：

  WO2005051298A3
• 作为产物：
  描述：

  4-苄氧基苯乙酰氯 生成 diethyl (4-benzyloxy)phenylacetyl phosphonate
  参考文献：
  名称：

  TERANISHI, MASAYUKI;TAKAHASHI, MITSURU;NOMOTO, HISAYO;KASE, HIROSHI;SHUTO+

  摘要：

  DOI：

文献信息

• Novel Phosphinic Acid-Containing Thyromimetics
  申请人：Erion Mark D.

  公开号：US20090028925A1

  公开（公告）日：2009-01-29

  The present invention relates to compounds of phosphonic acid-containing T3 mimetics and monoesters thereof, stereoisomers, pharmaceutically acceptable salts, co-crystals, and prodrugs thereof and pharmaceutically acceptable salts and co-crystals of the prodrugs, as well as their preparation and uses for preventing and/or treating metabolic diseases such as obesity, NASH, hypercholesterolemia and hyperlipidemia, as well as associated conditions such as atherosclerosis, coronary heart disease, impaired glucose tolerance, metabolic syndrome x and diabetes.

  本发明涉及含有磷酸基T3拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟
• Synthesis and Biological Evaluation of a Series of Liver-Selective Phosphonic Acid Thyroid Hormone Receptor Agonists and Their Prodrugs
  作者：Serge H. Boyer、Hongjian Jiang、Jason D. Jacintho、Mali Venkat Reddy、Haiqing Li、Wenyu Li、Jennifer L. Godwin、William G. Schulz、Edward E. Cable、Jinzhao Hou、Rongrong Wu、James M. Fujitaki、Scott J. Hecker、Mark D. Erion

  DOI：10.1021/jm800824d

  日期：2008.11.27

  Phosphonic acid (PA) thyroid hormone receptor (TR) agonists were synthesized to exploit the poor distribution of PA-based drugs to extrahepatic tissues and thereby to improve the therapeutic index. Nine PAs showed excellent TR binding affinities (TR beta(1), K-i < 10 nM), and most of them demonstrated significant cholesterol lowering effects in a cholesterol-fed rat (CFR) model. Unlike the corresponding carboxylic acid analogue and T-3, PA 22c demonstrated liver-selective effects by inducing maximal mitochondrial glycerol-3-phosphate dehydrogenase activity in rat liver while having no effect in the heart. Because of the low oral bioavailability of PA 22c, a series of prodrugs was synthesized and screened for oral efficacy in the CFR assay. The liver-activated cyclic 1-(3-chlorophenyl)-1,3-propanyl prodrug (MB07811) showed potent lipid lowering activity in the CFR (ED50 0.4 mg/kg, po) and good oral bioavailability (40%, rat) and was selected for development for the treatment of hypercholesterolemia.
• Identification of ACE pharmacophore in the phosphonopeptide metabolite K-26
  作者：Ioanna Ntai、Brian O. Bachmann

  DOI：10.1016/j.bmcl.2007.11.130

  日期：2008.5

  The naturally occurring phosphonotripeptide K-26 is a potent angiotensin converting enzyme (ACE) inhibitor containing an alpha-amino phosphonic acid analogue of tyrosine. Previous studies have demonstrated that canonical peptide analogues of K-26 are micromolar inhibitors of ACE. To ascertain the structure-activity relationships in this class of ACE inhibitory natural products, K-26 and eight analogues were chemically synthesized and evaluated. Phosphonyl substitution was found to be the critical determinant of activity, resulting in a 1500-fold increase in ACE inhibition versus carboxyl analogues. Secondarily, the absolute configuration of the terminal alpha-amino phosphonate and N-acetylation were found to significantly modulate ACE inhibitory activity. (c) 2007 Elsevier Ltd. All rights reserved.
• TERANISHI, MASAYUKI;TAKAHASHI, MITSURU;NOMOTO, HISAYO;KASE, HIROSHI;SHUTO+
  作者：TERANISHI, MASAYUKI、TAKAHASHI, MITSURU、NOMOTO, HISAYO、KASE, HIROSHI、SHUTO+

  DOI：——

  日期：——
• US4733000A
  申请人：——

  公开号：US4733000A

  公开（公告）日：1988-03-22