diethyl <3-<(p-tolylsulfonyl)oxo>propyl>phosphonate | 117144-99-7

• 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: diethyl <3-<(p-tolylsulfonyl)oxo>propyl>phosphonate
• 英文别名: diethyl <3-<(p-toluenesulfonyl)oxy>propyl>phosphonate；3-Diethoxyphosphorylpropyl 4-methylbenzenesulfonate
• CAS: 117144-99-7
• 化学式: C₁₄H₂₃O₆PS
• 分子量: 350.373
• InChiKey: XWQBSERRFHHCGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  87.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl <3-<(p-tolylsulfonyl)oxo>propyl>phosphonate 、 N-<<2-(trimethylsilyl)ethoxy>carbonyl>-trans-2-<(3E)-4,8-dimethyl-3,7-nonadienyl>-2-methyl-trans-3-<(1E,5E)-2,6,10-trimethyl-1,5,9-undecatrienyl>cyclopropylamine 在 potassium hydride 作用下， 生成 diethyl <3-carbonyl>-N--2-methyl-trans-3-<(1E,5E)-2,6,10-trimethyl-1,5,9-undecatrienyl>-1-cyclopropyl>amino>propyl>phosphonate
  参考文献：
  名称：

  Synthesis of ammonium analogs of carbocationic intermediates in the conversion of presqualene diphosphate to squalene

  摘要：

  DOI：

  10.1021/jo00260a019
• 作为产物：
  描述：

  3-(3-diethoxyphosphorylpropoxy)oxane 、 对甲苯磺酰氯 在 4-二甲氨基吡啶 、 4-甲基苯磺酸吡啶 作用下， 生成 diethyl <3-<(p-tolylsulfonyl)oxo>propyl>phosphonate
  参考文献：
  名称：

  Synthesis of ammonium analogs of carbocationic intermediates in the conversion of presqualene diphosphate to squalene

  摘要：

  DOI：

  10.1021/jo00260a019

文献信息

• Structure–function studies on nucleoside antibiotic mureidomycin A: synthesis of 5′-functionalised uridine models
  作者：Caragh A Gentle、Stephen A. Harrison、Masatoshi Inukai、Timothy D. H. Bugg

  DOI：10.1039/a901287g

  日期：——

  The importance of functional groups in nucleoside antibiotic mureidomycin A (MRD A) for biological activity has been examined by derivatisation of samples of the natural product, and by synthesis of uridine-containing analogues. N-Succinyl and di- and tri-acetyl derivatives MRD A have been prepared, and were found to have reduced activity as inhibitors of E. coli translocase I. The enamide alkene of MRD A was found to be extremely resistant towards hydrogenation by a variety of reagents. Several 5′-functionalised uridine derivatives were synthesised from N 3-p-methoxybenzyl-2′,3′-isopropylideneuridine. A series of 5′-aminoacyl derivatives were prepared, and the 3-aminopropionyl (IC50 260 µM) and 7-aminoheptanoyl (IC50 1.5 mM) derivatives were found to act as reversible inhibitors. An analogue mimicking the carboxy terminus of MRD A was synthesised, and also acted as an inhibitor of translocase I (IC50 1.9 mM). A phosphonate analogue designed as a possible suicide inhibitor showed modest inhibition (IC50 3.7 mM), which was shown to be irreversible.

  功能团在核苷类抗生素mureidomycin A (MRD A)生物活性中的重要性，通过对天然产物样品的衍生化和合成含尿苷类似物进行了研究。已制备N-琥珀酰和二、三乙酰衍生物MRD A，发现它们作为大肠杆菌转位酶I抑制剂的活性降低。MRD A的烯酰胺烯对多种试剂的氢化表现出极强的抗性。从N-3-对甲氧基苯甲基-2′,3′-异丙烯基尿苷合成了几种5′-功能化的尿苷衍生物。制备了一系列5′-氨酰衍生物，其中3-氨基丙酰基（IC50 260 μM）和7-氨基庚酸（IC50 1.5 mM）衍生物被发现作为可逆抑制剂。一种模仿MRD A羧基末端的类似物被合成，并且也作为转位酶I的抑制剂（IC50 1.9 mM）。一种设计为可能自杀抑制剂的磷onate类似物显示出适度抑制（IC50 3.7 mM），且被证明是不可逆的。
• CAPSON, TODD L.;THOMPSON, MICHAEL D.;DIXIT, VYAS M.;GAUGHAN, ROGER G.;POU+, J. ORG. CHEM., 53,(1988) N 25, C. 5903-5908
  作者：CAPSON, TODD L.、THOMPSON, MICHAEL D.、DIXIT, VYAS M.、GAUGHAN, ROGER G.、POU+

  DOI：——

  日期：——
• US5441946A
  申请人：——

  公开号：US5441946A

  公开（公告）日：1995-08-15
• US5563128A
  申请人：——

  公开号：US5563128A

  公开（公告）日：1996-10-08
• [EN] PHOSPHONATE DERIVATIVES OF LIPOPHILIC AMINES<br/>[FR] DERIVES PHOSPHONATE D'AMINES LIPOPHILES
  申请人：RHONE-POULENC RORER PHARMACEUTICALS INC.

  公开号：WO1995028155A1

  公开（公告）日：1995-10-26

  (EN) This invention relates to a class of novel phosphonate derivatives of lipophilic amines which exhibit squalene synthase inhibition properties. More specifically the compounds are bis aryl cycloalkylamino and azacycloalkyl phosphonates. Compounds of this invention reduce levels of serum cholesterol in the body without significantly reducing mevalonic metabolite synthesis. This invention relates also to pharmacological compositions and method of treatment for lowering serum cholesterol levels using the compounds of this invention.(FR) Cette invention concerne une classe de nouveaux dérivés phosphonate d'amines lipophiles qui présentent des propriétés d'inhibition de la squalène synthase, ces composés étant plus spécifiquement des phosphonates de bis aryle cycloalkylamino et d'azacycloalkyle. Les composés de cette invention diminuent les taux de cholestérol sérique dans le corps sans réduire significativement la synthèse de métabolite mévalonique. Cette invention concerne également des compositions pharmacologiques et un procédé de traitement visant à abaisser les taux de cholestérol sérique à l'aide des composés de l'invention.