H-Sta-OEt | 100002-32-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: H-Sta-OEt
• 英文别名: H-(SS)-Sta-OEt；ethyl (3S,4S)-4-amino-3-hydroxy-6-methylheptanoate
• CAS: 100002-32-2
• 化学式: C₁₀H₂₁NO₃
• 分子量: 203.282
• InChiKey: WHQQUBMCFYWHIS-IUCAKERBSA-N

物化性质

• 沸点：
  311.3±27.0 °C(Predicted)
• 密度：
  1.019±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  72.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  H-Sta-OEt 在 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 Boc-Sta-Ala-Sta-OEt
  参考文献：
  名称：

  高效合成不对称二取代的二茂铁：电化学双肽-Fc-生物传感器。

  摘要：

  电化学二肽-Fc-生物传感器，即非对称二取代的二茂铁（1a，1b），是通过直接合成方法由1,1'-二茂铁二羧酸合成的。另外，已经报道了五肽（2）的有效溶液合成。

  DOI：

  10.1016/s0040-4039(01)00251-9
• 作为产物：
  描述：

  (3S,4S)-ethyl 4-(tert-butoxycarbonylamino)-3-hydroxy-6-methylheptanoate 在 盐酸 作用下， 生成 H-Sta-OEt
  参考文献：
  名称：

  含有双[（1-萘基）甲基]乙酰基作为N末端成分的二肽肾素抑制剂

  摘要：

  描述了含有双[（1-萘基）甲基]乙酰基作为N-末端组分的有效的二肽肾素抑制剂的合成和生物学活性。

  DOI：

  10.1039/c39900001672

文献信息

• Dipeptide renin inhibitors containing a bis[(1-naphthyl)methyl]acetyl group as the N-terminal component
  作者：Takahide Nishi、Yasuhiro Morisawa、Yasuteru Lijima、Hiroyuki Koike、Yuichiro Yabe

  DOI：10.1039/c39900001672

  日期：——

  The syntheses and biological activities of potent dipeptide renin inhibitors containing a bis[(1-napthyl)methyl]acetyl group as the N-terminal component are described.

  描述了含有双[（1-萘基）甲基]乙酰基作为N-末端组分的有效的二肽肾素抑制剂的合成和生物学活性。
• New Renin Inhibitors with Pseudodipeptidic Units in P1-P1' and P2'-P3' Positions.
  作者：Ryszard Paruszewski、Pawel Jaworski、Iwona Winiecka、Jadwiga Tautt、Jadwiga Dudkiewicz

  DOI：10.1248/cpb.50.850

  日期：——

  A series of four new potential renin inhibitors has been synthesized. The structure of the compounds was designed in such a way as to produce agents resistant to enzymatic degradation, metabolically stable, possibly potent and with improved oral absorption. All positions of the 8—13 fragment of the human angiotensinogen were occupied by unnatural units (two unnatural amino acids in positions P3 and P2 and two pseudodipeptides in positions P1–P1′ and P2′–P3′). Both N- and C-terminal functions of the inhibitors were blocked with tert-Boc and ethyl ester groups. Their hydrophobicity evaluated as a log P value, calculated by a computer method, was 6.57 and 6.08 respectively. All peptides were obtained by the carbodiimide method in solution and purified by chromatography on the SiO2 column. Their resistance to enzymatic degradation was assayed by determination of stability against chymotrypsin activity. The potency was measured in vitro by a spectrofluorimetric method (assay of Leu-Val-Tyr-Ser released from the N-acetyltetradecapeptide substrate by renin in the presence of the inhibitor). All inhibitors were stable to chymotrypsin. Their IC50 (M/l) values were: 9.6×10−4 (12), 1.6×10−5 (17), 1.0×10−5 (22) and 1.0×10−5 (23) respectively.

  一系列四种新的潜在肾素抑制剂已被合成。这些化合物的结构经过精心设计，可产生抗酶降解、代谢稳定、可能有效且口服吸收改善的药物。人血管紧张素原8-13片段的所有位置都被非天然单位占据（P3和P2位上的两个非天然氨基酸和P1-P1'和P2'-P3'位上的两个假二肽）。抑制剂的 N 端和 C 端功能均被叔 Boc 和乙酯基团阻断。它们的疏水性通过计算机方法计算的log P值分别为6.57和6.08。所有肽均通过溶液中的碳二亚胺法获得，并通过 SiO2 柱色谱纯化。通过测定胰凝乳蛋白酶活性的稳定性来测定它们对酶促降解的抵抗力。通过荧光分光光度法在体外测量效力（在抑制剂存在下测定肾素从 N-乙酰基十四肽底物释放的 Leu-Val-Tyr-Ser）。所有抑制剂对胰凝乳蛋白酶均稳定。它们的IC50（M/l）值分别为：9.6×10−4（12）、1.6×10−5（17）、1.0×10−5（22）和1.0×10−5（23）。
• New renin-inhibitory peptides and their use
  申请人：Sankyo Company, Limited

  公开号：US04698329A1

  公开（公告）日：1987-10-06

  Compounds of formula R.sup.1 CO--NH--CH(R.sup.2)--CONH--CH(R.sup.3)--X [wherein: R.sup.1 represents alkyl having an .alpha.-amino or protected .alpha.-amino substituent and an aryl, heterocyclic or heterocyclic-dithio substituent; R.sup.2 represents a variety of aliphatic and cycloaliphatic hydrocarbon groups, which may be substituted; R.sup.3 represents isobutyl, sec-butyl, benzyl or (C.sub.3 -C.sub.8 cycloalkyl)methyl; and X represents a group of formula --CH(--A--R.sup.4)--Y (in which: A represents a single bond or an alkylene group; R.sup.4 represents a carboxy group; a protected carboxy group, a carbamoyl group, an N-substituted carbamoyl group, a carbazoyl group, an N-substituted carbazoyl group or an acyl group; and Y represents a hydroxy group, a mercapto group or a formyl group), or a group of formula --P(O) (R.sup.5)--OH (in which R.sup.5 represents a substituted alkyl group having at least one substituent selected from carboxy groups, protected carboxy groups, N-substituted carbamoyl groups, carbazoyl groups, N-substituted carbazoyl groups, C.sub.2 -C.sub.7 aliphatic carboxylic acyl groups and aromatic carboxylic acyl groups)]; and their salts are renin inhibitors, which may be used in the treatment of angiotensin-induced hypertension.

  化合物的化学式为R.sup.1 CO--NH--CH(R.sup.2)--CONH--CH(R.sup.3)--X [其中：R.sup.1代表具有.alpha.-氨基或受保护的.alpha.-氨基取代基和芳基，杂环或杂环-二硫取代基的烷基；R.sup.2代表多种脂肪族和环状脂肪族碳氢基团，可以被取代；R.sup.3代表异丁基，仲丁基，苄基或（C.sub.3-C.sub.8 环状烷基）甲基；X代表式--CH(--A--R.sup.4)--Y的基团（其中：A代表单键或烷基链；R.sup.4代表羧基，受保护的羧基，氨基甲酰基，N-取代的氨基甲酰基，氨基苯甲酰基，N-取代的氨基苯甲酰基或酰基；Y代表羟基，巯基或甲酰基），或式--P(O)(R.sup.5)--OH的基团（其中R.sup.5代表具有至少一个取代基的取代烷基，所述取代基从羧基，受保护的羧基，N-取代的氨基甲酰基，氨基苯甲酰基，N-取代的氨基苯甲酰基，C.sub.2-C.sub.7脂肪族羧酸酰基和芳香族羧酸酰基中选择）]；它们的盐是肾素抑制剂，可用于治疗肾素诱导的高血压。
• Polypeptide derivatives containing 5-amino-2,5-disubstituted-4-hydroxypentanoic acid residues
  申请人：PFIZER INC.

  公开号：EP0212903A2

  公开（公告）日：1987-03-04

  Polypeptide derivatives containing 5-amino-2,5-disubstituted-4-hydroxypentanoic acid residues are of the formula: wherein, for example in a preferred embodiment R is t-butyloxycarbonyl, m and n are each 0 or 1, their sum being at least 1; R is cyclohexylmethyl; R2 is 2-methylpropyl, 2-methyl-2--propenyl, benzyl, 4-chlorobenzyl, 3-chlorobenzyl, 4-methylbenzyl, 4-methoxybenzyl, 3,4-dichlorobenzyl, 2-chlorobenzyl or cyclohexylmethyl; R3 is hydrogen; R4 is hydrogen, methyl, 4-aminobutyl, 2-carboxyethyl, 3-(ethoxycarbonyl)propyl or 3-(benzyloxycarbonyl)propyl; W is phenylalanyl, W1 is histidyl and W2 is lysyl. These compounds are useful for inhibiting the angiotensinogen cleaving action of the enzyme renin having particular utility in the treatment of hypertension.

  含有 5-氨基-2,5-二取代-4-羟基戊酸残基的多肽衍生物为以下式子： 其中，例如在一个优选的实施方案中，R是叔丁氧羰基，m和n各为0或1，它们的总和至少为1；R是环己基甲基；R2是2-甲基丙基、2-甲基-2-丙烯基、苄基、4-氯苄基、3-氯苄基、4-甲基苄基、4-甲氧基苄基、3,4-二氯苄基、2-氯苄基或环己基甲基；R3 是氢；R4 是氢、甲基、4-氨基丁基、2-羧乙基、3-（乙氧基羰基）丙基或 3-（苄氧基羰基）丙基；W 是苯丙氨酰，W1 是组氨酰，W2 是赖氨酰。 这些化合物可用于抑制肾素酶的血管紧张素原裂解作用，特别适用于治疗高血压。
• Winiecka, Iwona; Dudkiewicz-Wilczynska, Jadwiga; Roman, Iza, Acta poloniae pharmaceutica, 2010, vol. 67, # 4, p. 367 - 374
  作者：Winiecka, Iwona、Dudkiewicz-Wilczynska, Jadwiga、Roman, Iza、Paruszewski, Ryszard

  DOI：——

  日期：——