2-benzyl-3-(tert-butylthio)propionic acid | 114469-27-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 2-benzyl-3-(tert-butylthio)propionic acid
• 英文别名: 2-Benzyl-3-tert-butylsulfanylpropanoic acid
• CAS: 114469-27-1
• 化学式: C₁₄H₂₀O₂S
• 分子量: 252.378
• InChiKey: ZJSKUSHWHUPXII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-benzyl-3-(tert-butylthio)propionic acid 在 oxone 作用下， 以 甲醇 、 水 为溶剂， 以82%的产率得到2-benzyl-3-(tert-butylsulfonyl)propionic acid
  参考文献：
  名称：

  Propargyl-terminated cycloalkylalkyl-P2-site substituted

  摘要：

  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。

  公开号：

  US05268391A1
• 作为产物：
  描述：

  乙基2-苄基丙烯酸酯 在 氢氧化钾 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 72.0h， 生成 2-benzyl-3-(tert-butylthio)propionic acid
  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

文献信息

• Renin-inhibiting functionalized peptidyl aminodiols and - triols
  申请人：ABBOTT LABORATORIES

  公开号：EP0341602A2

  公开（公告）日：1989-11-15

  A renin inhibiting compound of the formula: or a pharmaceutically acceptable salt, ester or prodrug thereof.

  一个公式为的抑制肾素的化合物： 或其药用可接受的盐、酯或前药。
• Peptidyl difluorodiol renin inhibitors
  申请人：ABBOTT LABORATORIES

  公开号：EP0416393A1

  公开（公告）日：1991-03-13

  A renin inhibiting compound of the formula: wherein A is a functional group; W is (1) -C(O)-, (2) -CH(OH)- or (3) -N(R₂)- wherein R₂ is hydrogen or loweralkyl; U is (1) -C(O)-, (2) -CH₂- or (3) -N(R₂)- wherein R₂ is hydrogen or lower alkyl, with the proviso that when W is -CH(OH)- then U is -CH₂- and with the proviso that U is -C(O)- or -CH₂- when W is -N(R₂)-; V is (1) -CH-, (2) -C(OH)- or (3) -C(halogen)- with the proviso that v is -CH-­when U is -N(R₂)-; Q is -CH(R₁)- or -C(=CHR1a)- wherein R₁ is (1) loweralkyl, (2) cycloalkylalkyl, (3) arylalkyl, (4) (heterocyclic)alkyl, (5) 1-benzyloxyethyl, (6) phenoxy, (7) thiophenoxy or (8) anilino, provided that B is -CH₂- or -CH(OH)- or A is hydrogen when R₁ is phenoxy, thiophenoxy or anilino and R1a is aryl or heterocyclic; R₃ is a functional group; R₄ is (1) loweralkyl, (2) cycloalkylmethyl or (3) benzyl; R₅ is -CH(OH)- or -C(O)-; R₆ is -CH(OH)- or -C(O)-; and Z is (1) lower alkyl, (2) aryl, (3) arylalkyl, (4) cycloalkyl, (5) cycloalkylalkyl, (6) heterocyclic or (7) (heterocyclic)alkyl; or a pharmaceutically acceptable salt, ester or prodrug thereof.

  一种肾素抑制化合物的化学式：其中A是一个功能基团；W是(1) -C(O)-，(2) -CH(OH)-或(3) -N(R₂)-，其中R₂是氢或较低烷基；U是(1) -C(O)-，(2) -CH₂-或(3) -N(R₂)-，其中R₂是氢或较低烷基，但当W为-CH(OH)-时，则U为-CH₂-，并且当U为-N(R₂)-时，U为-C(O)-或-CH₂-；V是(1) -CH-，(2) -C(OH)-或(3) -C(卤素)-，但当U为-N(R₂)-时，V为-CH-；Q是-CH(R₁)-或-C(=CHR1a)-，其中R₁是(1) 较低烷基，(2) 环烷基烷基，(3) 芳基烷基，(4) (杂环)烷基，(5) 1-苄氧乙基，(6) 苯氧基，(7) 噻吩氧基或(8) 氨基苯基，前提是当R₁是苯氧基、噻吩氧基或氨基苯基时，B是-CH₂-或-CH(OH)-，或A是氢，而R1a是芳基或杂环；R₃是一个功能基团；R₄是(1) 较低烷基，(2) 环烷基甲基或(3) 苄基；R₅是-CH(OH)-或-C(O)-；R₆是-CH(OH)-或-C(O)-；Z是(1) 较低烷基，(2) 芳基，(3) 芳基烷基，(4) 环烷基，(5) 环烷基烷基，(6) 杂环或(7) (杂环)烷基；或其药学上可接受的盐、酯或前药。
• Synthesis of tritium labelled thiorphan, an enkephalinase inhibitor
  作者：Shao-Yong Wu、Mohammad R. Masjedizadeh

  DOI：10.1002/jlcr.1566

  日期：2009.1

  Tritium labelling of the enkephalinase inhibitor, thiorphan, is complicated by the presence of mercapto functional group. Reactions often used in aromatic tritiation, such as halogination and catalytic halogen/tritium displacement, are adversely affected by the presence of the divalent sulfur moeity. By protecting the SH group with t-butyl group, the tritiation reaction proceeded smoothly without catalyst

  由于巯基官能团的存在，脑啡肽酶抑制剂噻吩的氚标记变得复杂。常用于芳族氚化的反应，如卤化和催化卤素/氚置换，受到二价硫部分存在的不利影响。通过用叔丁基保护 SH 基团，氚化反应顺利进行，没有催化剂中毒。使用 2-硝基苯亚磺酰氯和二硫苏糖醇 (DTT) 可以轻松高效地重新生成巯基官能团。如此获得的[ 3 H]-噻吩通过AN-HPLC具有>99%的放射化学纯度和18.42Ci/mmol的比活。[3H]-噻吩在 4°C 下储存在含有 10% 甲醇和 0.2% DTT 的水溶液中避光时表现出良好的稳定性。版权所有 © 2008 John Wiley & Sons, Ltd.
• Antihypertensive 5-amino-4-hydroxyvaleryl derivatives substituted by
  申请人：Ciba-Geigy Corporation

  公开号：US04758584A1

  公开（公告）日：1988-07-19

  Compounds of the formula ##STR1## in which R.sub.1 represents acyl substituted by a thio, sulphinyl or sulphonyl group, A represents an optionally N-alkylated .alpha.-amino acid residue that is bonded N-terminally to R.sub.1 and C-terminally to the group --NR.sub.2 --, R.sub.2 represents hydrogen or lower alkyl, R.sub.3 represents hydrogen, lower alkyl, optionally etherified or esterified hydroxy-lower alkyl, cycloalkyl, cycloalkyl-lower alkyl, bicycloalkyl-lower alkyl, tricycloalkyl-lower alkyl, aryl or aryl-lower alkyl, R.sub.4 represents hydroxy or etherified or esterified hydroxy, R.sub.5 represents lower alkyl, optionally etherified or esterified hydroxy-lower alkyl, cycloalkyl, cycloalkyl-lower alkyl, bicycloalkyl, bicycloalkyl-lower alkyl, tricycloalkyl, tricycloalkyl-lower alkyl, aryl, aryl-lower alkyl, optionally substituted carbamoyl, optionally substituted amino, optionally substituted hydroxy, optionally substituted mercapto, sulphinyl or sulphonyl, and R.sub.6 represents substituted amino, and salts of such compounds having salt-forming groups, inhibit the blood pressure-increasing action of the enzyme renin and can be used as anti-hypertensives.

  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
• 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。