N-[N-[(1,1-Dimethylethoxy)carbonyl]-L-alanyl]-N-methylglycine | 126307-30-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: N-[N-[(1,1-Dimethylethoxy)carbonyl]-L-alanyl]-N-methylglycine
• 英文别名: Boc-alanylsarcosine；Boc-Ala-Sar-OH；2-[methyl-[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]acetic acid
• CAS: 126307-30-0
• 化学式: C₁₁H₂₀N₂O₅
• 分子量: 260.29
• InChiKey: ZYTWVMYBKUNPIN-ZETCQYMHSA-N

物化性质

• 沸点：
  434.0±30.0 °C(Predicted)
• 密度：
  1.173±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  95.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[N-[(1,1-Dimethylethoxy)carbonyl]-L-alanyl]-N-methylglycine 以85%的产率得到
  参考文献：
  名称：

  SEEBACH, DIETER;BOSSLER, HANS;GRUNDLER, HANSJORG;SHODA, SHIN-ICHIRO;WENGE+, HELV. CHIM. ACTA, 74,(1991) N, C. 197-224

  摘要：

  DOI：
• 作为产物：
  描述：

  Boc-Ala-Sar-OCH2Ph 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 14.0h， 以99%的产率得到N-[N-[(1,1-Dimethylethoxy)carbonyl]-L-alanyl]-N-methylglycine
  参考文献：
  名称：

  通过含有肌氨酸锂醇单元的多官能化和LiCl溶剂化的衍生物的C烷基化

  摘要：

  三肽和六肽衍生物Boc-Gly-Sar-MeLeu-OH（5b），Boc-Ala-Sar-Sar-OH（6b），Boc-Ala-Sar-MeLeu-OH（7b）和Boc-Abu-Sar -OH -MeLeu-Val-MeLeu-Ala-OH（12b）可以被多去质子化（分别为三硫代和五硫代衍生物K和P），并因此在肌氨酸（Sar）部分上用MeI和烯丙基或PhCH 2 Br进行C-烷基化。将多晶化的物质溶解在THF中，并通过添加过量的碱（二异丙基氨基锂（LDA）），添加的LiCl和/或助溶剂N，N来改变其反应活性。′-二甲基丙烯脲（DMPU）。优化7b（表3）和12b（方案8）情况下的甲基化反应条件，得到的产物中，离析物的Sar残基已转化为Me-D-Ala单元，产率为80（9c / 8c）和67％（14c / 13c），非对映选择性约为ca。4：1。三肽5b和6b仅包含一个立体生成中心，观察到选

  DOI：

  10.1002/hlca.19910740121

文献信息

• Phosphonamidate compounds
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04432971A1

  公开（公告）日：1984-02-21

  Phosphonamidates of the formula ##STR1## wherein X is a substituted or unsubstituted imino or amino acid or ester. These compounds possess angiotensin converting enzyme activity and are thus useful as hypotensive agents.

  式中X为取代或未取代的亚胺基或氨基酸或酯。这些化合物具有血管紧张素转化酶活性，因此可用作降压剂。
• Elektrochemische Decarboxylierung vonL.-Threonin- und Oligopeptid-Derivaten unter Bildung vonN-Acyl-N, O-acetalen: Herstellung von Oligopeptiden mit Carboxamid-oder Phosphonat-C-Terminus
  作者：Dieter Seebach、Roland Charczuk、Christian Gerber、Philippe Renaud、Heinz Berner、Helmut Schneider

  DOI：10.1002/hlca.19890720302

  日期：1989.5.3

  Electrochemical Decarboxylation of L-Threonine and Oligopeptide Derivatives with Formation of N-Acyl-N, O-acetals: Preparation of Oligopeptides with Amide or Phophonate C-Terminus

  L-苏氨酸和寡肽衍生物的电化学脱羧反应，形成N-酰基-N，O-乙缩醛：酰胺或膦C-末端制备寡肽
• Dehydrooligopeptides. XIV. Convenient Coupling of<i>N</i>-Carboxy-<i>α</i>-dehydroamino Acid Anhydride with Both Amine and Carboxyl Components
  作者：Chung-gi Shin、Seiji Honda、Katsuhiro Morooka、Yasuchika Yonezawa

  DOI：10.1246/bcsj.66.1844

  日期：1993.6

  usefulness of N-carboxy-α-dehydroamino acid anhydride (ΔNCA), the optimum conditions of the acylation of ΔNCA with N-protected α-amino acids (AA) were thoroughly examined. Furthermore, various kinds of AA or dipeptides as a C-component were utilized in the acylation of ΔNCA, followed by condensation with an AA methyl ester as an N-component.

  为了进一步开发和扩大N-羧基-α-脱氢氨基酸酐（ΔNCA）的用途，对ΔNCA与N-保护的α-氨基酸（AA）酰化的最佳条件进行了彻底检查。此外，在ΔNCA的酰化中利用各种AA或二肽作为C-组分，然后与作为N-组分的AA甲酯缩合。
• SERIES OF HALOGENATED TETRACYCLIC TRITERPENE DERIVATIVES AND THEIR PREPARATION AND APPLICATION
  申请人：SHANGHAI KING-X BIOTECH CO., LTD

  公开号：US20220177511A1

  公开（公告）日：2022-06-09

  The invention provides a series of halogenated tetracyclic triterpene derivatives and their preparation and application. It is represented by the following general structural formula: R 1 is halogen, R 2 is H, and the halogen is selected from fluorine, chlorine, bromine or iodine; or R 1 and R 2 are each fluorine, and R 3 is an amine, alcohol, amino acid, peptide or phosphate linked to oxygen through an acyl group. The derivatives are relatively stable in rat whole blood through pharmacokinetic studies. The absolute bioavailability after a single intragastric administration for male and female rats was 15.6% and 28.4% respectively. The mean bioavailability was 22%. The derivatives showed better in vivo activities compared with the existing standard drugs enalapril and sacubitril valsartan sodium. Meanwhile, hydrophilic prodrugs of the tetracyclic triterpenoid derivatives in the present invention were prepared. The derivatives of the present invention can be used for preparing cardiovascular medicines.

  本发明提供了一系列卤代四环三萜衍生物及其制备和应用。其通式如下：R1为卤素，R2为氢，卤素选自氟、氯、溴或碘；或R1和R2均为氟，R3为胺、醇、氨基酸、肽或磷酸，通过酰基连接到氧。通过药代动力学研究，这些衍生物在大鼠全血中相对稳定。单次口服给雄性和雌性大鼠后的绝对生物利用度分别为15.6％和28.4％。平均生物利用度为22％。与现有标准药物依那普利和沙库巴曲钠相比，这些衍生物在体内活性更好。同时，本发明还制备了四环三萜衍生物的亲水性前药。本发明的衍生物可用于制备心血管药物。
• HALOGENATED TETRACYCLIC TRITERPENE DERIVATIVE, PREPARATION AND APPLICATION THEREOF
  申请人：Shanghai King-X Biotech Co., Ltd.

  公开号：EP4043447A1

  公开（公告）日：2022-08-17

  The invention provides a series of halogenated tetracyclic triterpene derivatives and their preparation and application. It is represented by the following general structural formula: wherein R1 is halogen, R2 is H, and the halogen is selected from fluorine, chlorine, bromine or iodine; or R1 and R2 are each fluorine, and R3 is an amine, alcohol, amino acid, peptide or phosphate linked to oxygen through an acyl group. The derivatives of the present invention are relatively stable in rat whole blood through pharmacokinetic studies. The absolute bioavailability after a single intragastric administration for male and female rats was 15.6% and 28.4% respectively. The mean bioavailability was 22%. The derivatives of the present invention showed better in vivo activities compared with the existing standard drugs enalapril and sacubitril valsartan sodium. Meanwhile, hydrophilic prodrugs of the tetracyclic triterpenoid derivatives in the present invention were prepared, which improved the solubility and had better drug-likeness properties. The derivatives of the present invention can be used for preparing cardiovascular medicines and have great application value.

  本发明提供了一系列卤代四环三萜衍生物及其制备和应用。其结构通式如下： 其中 R1 为卤素，R2 为 H，卤素选自氟、氯、溴或碘；或 R1 和 R2 各为氟，R3 为通过酰基与氧相连的胺、醇、氨基酸、肽或磷酸。 通过药代动力学研究，本发明的衍生物在大鼠全血中相对稳定。雄性和雌性大鼠一次胃内给药后的绝对生物利用度分别为 15.6% 和 28.4%。平均生物利用率为 22%。与现有的标准药物依那普利和沙库比妥缬沙坦钠相比，本发明的衍生物显示出更好的体内活性。同时，本发明中四环三萜类衍生物亲水性原药的制备，提高了溶解度，具有更好的药物相似性。本发明的衍生物可用于制备心血管药物，具有很大的应用价值。