(αr)-α-[[(1,1-二甲基乙氧基)羰基]氨基]-苯戊酸 | 156130-68-6

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 其他氨基酸衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (αr)-α-[[(1,1-二甲基乙氧基)羰基]氨基]-苯戊酸
• 中文别名: (R)-2-叔丁氧羰基氨基-5-苯戊酸
• 英文名称: 2-(tert-butoxycarbonylamino)-5-phenyl-D-pentanoic acid
• 英文别名: (2R)-2-[(1,1-dimethylethoxy)carbonyl]amino-5-phenylpentanoic acid；(R)-2-tert-butoxycarbonylamino-5-phenylpentanoic acid；(R)-2-((tert-Butoxycarbonyl)amino)-5-phenylpentanoic acid；(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-phenylpentanoic acid
• CAS: 156130-68-6
• 化学式: C₁₆H₂₃NO₄
• 分子量: 293.363
• InChiKey: AIFKBFKJMQTYAM-CYBMUJFWSA-N

物化性质

• 沸点：
  480.2±45.0 °C(Predicted)
• 密度：
  1.121

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  (αr)-α-[[(1,1-二甲基乙氧基)羰基]氨基]-苯戊酸 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 醋酸异丙酯 、 水 为溶剂， 生成 (R)-2-Amino-5-phenyl-pentanoic acid [5-(4-chloro-phenyl)-3,3-dimethyl-1,1-dioxo-2,3-dihydro-1H-1λ⁶-isothiazol-4-ylmethyl]-ethyl-amide
  参考文献：
  名称：

  Structure activity studies of the serine-AIB dipeptide domain in 2,3-dihydroisothiazole based growth hormone secretagogues

  摘要：

  A series of growth hormone secretagogues (GHSs) based on 2,3-dihydroisothiazole has been synthesized in the search for a potential treatment of growth hormone deficiency or frailty in the elderly. This paper describes the evaluation of the SAR of the benzyl-D-Ser-aminoisobutyric acid dipeptide fragment. Introduction of substituents in the peptide backbone and in the phenyl ring has been investigated, as well as replacements for the benzyl group and for the AIB residue. A number of modifications resulted in enhanced potency over the parent benzyl-D-Ser-AIB derivative. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.07.070
• 作为产物：
  描述：

  D-N-acetyl-2-amino-5-phenylpentanoic acid 在 盐酸 、 sodium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 45.0h， 生成 (αr)-α-[[(1,1-二甲基乙氧基)羰基]氨基]-苯戊酸
  参考文献：
  名称：

  Structure activity studies of the serine-AIB dipeptide domain in 2,3-dihydroisothiazole based growth hormone secretagogues

  摘要：

  A series of growth hormone secretagogues (GHSs) based on 2,3-dihydroisothiazole has been synthesized in the search for a potential treatment of growth hormone deficiency or frailty in the elderly. This paper describes the evaluation of the SAR of the benzyl-D-Ser-aminoisobutyric acid dipeptide fragment. Introduction of substituents in the peptide backbone and in the phenyl ring has been investigated, as well as replacements for the benzyl group and for the AIB residue. A number of modifications resulted in enhanced potency over the parent benzyl-D-Ser-AIB derivative. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.07.070

文献信息

• Substituted bridged phenyl piperidines: orally active growth hormone secretagogues
  作者：Zhijian Lu、James R. Tata、Kang Cheng、Liente Wei、Wanda W.-S. Chan、Bridget Butler、Klaus D. Schleim、Thomas M. Jacks、Gerard Hickey、Arthur A. Patchett

  DOI：10.1016/s0960-894x(03)00261-0

  日期：2003.5

  A new series of growth hormone secretagogues have been discovered. The best compound, 26j, shows excellent ability to release growth hormone both in vitro and in vivo. The synthesis and biological activity of these compounds are discussed.

  已经发现了一系列新的生长激素促分泌素。最好的化合物26j在体外和体内均显示出出色的释放生长激素的能力。讨论了这些化合物的合成和生物活性。
• [EN] DITERPENOID COMPOUNDS THAT ACT ON PROTEIN KINASE C (PKC)<br/>[FR] COMPOSÉS DITERPÉNOÏDES AGISSANT SUR LA PROTÉINE KINASE C (PKC)
  申请人：K GEN INC

  公开号：WO2021062030A1

  公开（公告）日：2021-04-01

  This present disclosure relates to protein kinase C (PKC) modulating compounds, methods of treating a subject with cancer using the compounds, and combination treatments with a second therapeutic agent.

  本公开涉及蛋白激酶C（PKC）调节化合物，使用这些化合物治疗癌症患者的方法，以及与第二治疗剂联合治疗的方法。
• Synthesis and biological activities of phenyl piperazine- based peptidomimetic growth hormone secretagogues
  作者：Khaled J. Barakat、Kang Cheng、Wanda W.-S. Chan、Bridget S. Butler、Thomas M. Jacks、Klaus D. Schleim、Donald F. Hora、Gerard J. Hickey、Roy G. Smith、Arthur A. Patchett、Ravi P. Nargund

  DOI：10.1016/s0960-894x(98)00238-8

  日期：1998.6

  A new class of potent, orally active phenyl piperazine-based GH secretagogues have been discovered from attempts to mimic the arrangement of the phenyl substituent in the spiroindanyl piperidine and spiroindoline sulfonamide privileged structures of 4 and 1, respectively. The best of these compounds, 18 (EC50 = 2.8 nM) is nearly as potent as MK-0677 for releasing GH from rat pituitary cells.

  通过尝试模仿分别为4和1的螺二氢茚基哌啶和螺二氢吲哚磺酰胺特权结构中的苯基取代基排列，发现了一种新型的，基于口服活性的苯基哌嗪基的GH促分泌剂。这些化合物中最好的18种（EC50 = 2.8 nM）几乎可以与MK-0677一样有效地从大鼠垂体细胞释放GH。
• Synthesis and biological activities of spiroheterocyclic growth hormone secretagogues
  作者：Meng-Hsin Chen、Patrick P. Pollard、Arthur A. Patchett、Kang Cheng、Liente Wei、Wanda W.-S. Chan、Bridget Butler、Thomas M. Jacks、Roy G. Smith

  DOI：10.1016/s0960-894x(99)00183-3

  日期：1999.5

  The synthesis and biological activities of a series of spiroheterocyclic growth hormone secretagogues are reported. Modification of the spiroindane part-structure of the prototypal secretagogue L-162,752 revealed that the spiroindane could be replaced with spirobenzodihydrothiophen derivatives to enhance not only in vitro potency but also oral activity. In this study non-aromatic D-2-amino-4-cyclohexylbutanoic

  报道了一系列螺杂环生长激素促分泌剂的合成和生物学活性。原型促分泌素L-162,752的螺茚满烷部分结构的修饰表明，可用螺苯并二氢噻吩衍生物代替螺茚满，不仅可以增强体外效力，而且还可以增强口服活性。在这项研究中，非芳香族D-2-氨基-4-环己基丁酸类似物（8a-8d）也被确定为活性促泌剂。
• Highly potent growth hormone secretagogues
  作者：Zhijian Lu、James R. Tata、Kang Cheng、Liente Wei、Wanda W.-S. Chan、Bridget Butler、Klaus D. Schleim、Thomas M. Jacks、Gerard Hickey、Arthur A. Patchett

  DOI：10.1016/j.bmcl.2007.04.050

  日期：2007.7

  During an effort to search for more potent growth hormone secretagogues, we discovered a class of compounds of which the best compound 8 was 7-fold more active in vitro than the best compound in the series we revealed before [Tata, J. R.; Lu, Z.; Jacks, T. M.; Schleim, K. D.; Cheng, K.; Wei, L.; Chan, W.-S.; Butler, B.; Tsou, N.; Leung, K.; Chiu, S.-H. L.; Hickey, G. J.; Smith, R. G.; Patchett, A.

  在寻找更有效的生长激素促分泌素的过程中，我们发现了一类化合物，其中最佳化合物8的体外活性比我们之前揭示的系列最佳化合物高7倍。陆志; 杰克（TM）；Klech Schleim；Cheng K .; 魏升; Chan W.-S .; 巴特勒B. Tsou，N .；梁K. Chiu，S.-HL; Gic的Hickey；RG，史密斯；机管局，AA Bioorg。中 化学 Lett.1997，7，2319.]。动物研究表明，化合物8可以以低至0.06mpk的口服剂量刺激生长激素的释放。讨论了化学和生物学研究。