α-[[(1,1-dimethylethyl)-thio]methyl]benzenepropanoic acid,ethyl ester | 114469-29-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: α-[[(1,1-dimethylethyl)-thio]methyl]benzenepropanoic acid,ethyl ester
• 英文别名: 2-benzyl-3-tert-butylthio-propionic acid ethyl ester；α-[[(1,1-dimethylethyl)-thio]methyl]benzenepropanoic acid, ethyl ester；2-benzyl-3-tert.-butylthio-propionic acid ethyl ester；Ethyl 2-benzyl-3-tert-butylsulfanylpropanoate
• CAS: 114469-29-3
• 化学式: C₁₆H₂₄O₂S
• 分子量: 280.431
• InChiKey: HBIBSEHLDQEOAP-UHFFFAOYSA-N

物化性质

• 沸点：
  379.5±35.0 °C(Predicted)
• 密度：
  1.030±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  α-[[(1,1-dimethylethyl)-thio]methyl]benzenepropanoic acid,ethyl ester 在 oxone 作用下， 反应 15.0h， 以91.8 g的产率得到ethyl 2-benzyl-3-(tert-butylsulfonyl)propionate
  参考文献：
  名称：

  Synthesis and biological activity of some transition-state inhibitors of human renin

  摘要：

  A series of renin inhibitors containing the dipeptide transition state mimics (2S,4S,5S)-5-amino-4-hydroxy-2-isopropyl-7-methyloctanoic acid (Leu (OH)/Val) and (2S,4S,5S)-5-amino-4-hydroxy-2-isopropyl-6-cyclohexylhexanoic acid (CHa /(OH)/Val) was prepared. A structure-activity study with Boc-Phe-His-Leu (OH)/Val-Ile-His-NH2 (8a) as starting material led to N-[(2S)-2-[(tert-butylsulfonyl)methyl]-3-phenylpropionyl]-His-Cha (OH)/ Val- NHC4H9-n (8i) which has the length of a tetrapeptide and contains only one natural amino acid. Compound 8i had an IC50 of 2 x 10(-9) M against human renin and showed high enzyme specificity; IC50 values against the related aspartic proteinases pepsin and cathepsin D were (8 x 10(-6) and 3 x 10(-6) M, respectively). In salt-depleted marmosets, 8i inhibited plasma renin activity PRA and lowered blood pressure for up to 2 h after oral administration of a dose of 10 mg/kg.

  DOI：

  10.1021/jm00117a027
• 作为产物：
  描述：

  乙基2-苄基丙烯酸酯 、 叔丁基硫醇 以 四氢呋喃 为溶剂， 以68%的产率得到α-[[(1,1-dimethylethyl)-thio]methyl]benzenepropanoic acid,ethyl ester
  参考文献：
  名称：

  Antihypertensive 5-amino-4-hydroxyvaleryl derivatives substituted by

  摘要：

  公式为##STR1##的化合物，其中R.sub.1代表由硫、亚硫氧或磺酰基取代的酰基，A代表一个可选择地N-烷基化的α-氨基酸残基，该残基在N-端与R.sub.1和C-端与基团--NR.sub.2--键合，R.sub.2代表氢或较低的烷基，R.sub.3代表氢、较低的烷基、可选择地醚化或酯化的羟基较低烷基、环烷基、环烷基较低烷基、双环烷基较低烷基、三环烷基较低烷基、芳基或芳基较低烷基，R.sub.4代表羟基或醚化或酯化的羟基，R.sub.5代表较低的烷基、可选择地醚化或酯化的羟基较低烷基、环烷基、环烷基较低烷基、双环烷基、双环烷基较低烷基、三环烷基、三环烷基较低烷基、芳基、芳基较低烷基、可选择地取代的氨基甲酰、可选择地取代的氨基、可选择地取代的羟基、可选择地取代的巯基、亚硫

  公开号：

  US04758584A1

文献信息

• Diol sulfonamide and sulfinyl renin inhibitors
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US05098924A1

  公开（公告）日：1992-03-24

  Compounds of the formula ##STR1## wherein Z is SO or SO.sub.2 possess renin inhibition activity and are useful in treating hypertension and other diseases where the reduction of the levels of circulating angiotensin II are beneficial.

  式为##STR1##的化合物，其中Z为SO或SO.sub.2，具有抑制肾素活性的作用，并可用于治疗高血压和其他减少循环中抗肾素II水平有益的疾病。
• Cyclopropyl-alanine aryl/alkylsulfide/sulfonyl-terminated amino-diol
  申请人：G. D. Searle & Co.

  公开号：US05317039A1

  公开（公告）日：1994-05-31

  Compounds characterized generally as cyclopropyl alanine aryl/alkylsulfide/sulfonyl-terminated amino diol derivatives are useful as renin inhibitors for the treatment of hypertension. Compounds of particular interest are those of the formula ##STR1## wherein R.sup.1 is selected from isopropyl, isobutyl, sec-butyl, tert-butyl, phenyl, fluorophenyl, chlorophenyl, benzyl, fluorobenzyl, chlorobenzyl, naphthyl, fluoronaphthyl, chloronaphthyl, fluoronapthylmethyl and chloronaphthylmethyl; wherein x is zero or two; wherein R.sup.2 is selected from hydrido, methyl, ethyl and phenyl; wherein R.sup.3 is selected from hydrido, cyclohexylmethyl, benzyl, fluorobenzyl, chlorobenzyl, fluoronaphthylmethyl and chloronaphthylmethyl; wherein R.sup.5 is cyclopropylmethyl wherein R.sup.7 is cyclohexylmethyl; and wherein R.sup.8 is selected from n-propyl, isobutyl, cyclopropyl, cyclopropylmethyl, allyl and vinyl.

  通常被表征为环丙基丙氨酸芳基/烷基硫醚/磺酰基末端氨基二醇衍生物的化合物可用作治疗高血压的肾素抑制剂。特别感兴趣的化合物是具有以下结构的化合物：其中R.sup.1从异丙基、异丁基、仲丁基、叔丁基、苯基、氟苯基、氯苯基、苄基、氟苄基、氯苄基、萘基、氟萘基、氯萘基、氟萘基甲基和氯萘基甲基中选择；其中x为零或二；其中R.sup.2从氢、甲基、乙基和苯中选择；其中R.sup.3从氢、环己基甲基、苄基、氟苄基、氯苄基、氟萘基甲基和氯萘基甲基中选择；其中R.sup.5为环丙基甲基，其中R.sup.7为环己基甲基；其中R.sup.8从正丙基、异丁基、环丙基、环丙基甲基、烯丙基和乙烯中选择。
• Propargyl-terminated cycloalkylalkyl-P2-site substituted
  申请人：C. D. Searle & Co.

  公开号：US05268391A1

  公开（公告）日：1993-12-07

  Compounds characterized generally as being propargyl-terminated aryl/alkylsulfonyl-terminated amino diol derivatives having a cycloalkylalkyl group at the P2 substitution site are useful as renin inhibitors for the treatment of hypertension. Compounds of particular interest are those of the formula ##STR1## wherein R.sup.1 is selected from isopropyl, isobutyl, sec-butyl, tert-butyl, phenyl, fluorophenyl, chlorophenyl, benzyl, fluorobenzyl, chlorobenzyl, naphthyl, fluoronaphthyl, chloronaphthyl, fluoronaphthylmethyl and chloronaphthylmethyl; wherein R.sup.2 is selected from hydrido, methyl, ethyl and phenyl; wherein R.sup.3 is selected from hydrido, cyclohexylmethyl, benzyl, fluorobenzyl, chlorobenzyl, fluoronaphthylmethyl and chloronaphthylmethyl; wherein R.sup.5 is selected from cycloalkylalkyl groups containing from three to about twelve carbon atoms; wherein R.sup.7 is cyclohexylmethyl; and wherein R.sup.8 is propargyl or a propargyl-containing moiety.

  被普遍描述为具有在P2取代位点处具有环烷烃基的丙炔基结尾芳基/烷基磺酰基结尾氨基二醇衍生物的化合物被用作治疗高血压的肾素抑制剂。特别感兴趣的化合物是具有以下结构的那些化合物： 其中R1从异丙基、异丁基、仲丁基、叔丁基、苯基、氟苯基、氯苯基、苄基、氟苄基、氯苄基、萘基、氟萘基、氯萘基、氟萘基甲基和氯萘基甲基中选择；其中R2从氢、甲基、乙基和苯基中选择；其中R3从氢、环己基甲基、苄基、氟苄基、氯苄基、氟萘基甲基和氯萘基甲基中选择；其中R5从含有三至约十二个碳原子的环烷烃基中选择；其中R7是环己基甲基；其中R8是丙炔基或含丙炔基的基团。
• BUHLMAYER, PETER;CASELLI, ANTHONY;FUHRER, WALTER;GOSCHKE, RICHARD;RASETTI+, J. MED. CHEM., 31,(1988) N 9, C. 1839-1846
  作者：BUHLMAYER, PETER、CASELLI, ANTHONY、FUHRER, WALTER、GOSCHKE, RICHARD、RASETTI+

  DOI：——

  日期：——
• BUHLMAYER, PETER;STANTON, JAMES L.;FUHRER, WALTER;GOSCHKE, RICHARD;RASETT+
  作者：BUHLMAYER, PETER、STANTON, JAMES L.、FUHRER, WALTER、GOSCHKE, RICHARD、RASETT+

  DOI：——

  日期：——