(S)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-aminobutanoic acid | 117106-22-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (S)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-aminobutanoic acid
• 英文别名: H-Dab(Fmoc)-OH；(2S)-2-amino-4-(9H-fluoren-9-ylmethoxycarbonylamino)butanoic acid
• CAS: 117106-22-6
• 化学式: C₁₉H₂₀N₂O₄
• 分子量: 340.379
• InChiKey: SWKHFSHBIZGRLP-KRWDZBQOSA-N

物化性质

• 熔点：
  166 °C
• 沸点：
  596.2±50.0 °C(Predicted)
• 密度：
  1.294±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  102
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-aminobutanoic acid 生成 (S)-2-(Boc-氨基)-4-(Fmoc-氨基)丁酸
  参考文献：
  名称：

  GALPIN, IAN JAMES

  摘要：

  DOI：
• 作为产物：
  描述：

  (S)-2-(Boc-氨基)-4-(Fmoc-氨基)丁酸 在 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.0h， 生成 (S)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-aminobutanoic acid
  参考文献：
  名称：

  L-dabPNA和aegPNA之间形成复杂的证据。

  摘要：

  继续我们作为生物医学和生物工程应用的ODN类似物开发核苷酸的研究，在此我们报告基于l-二氨基丁酸（l-DABA）主链（dabPNA）的高腺嘌呤六聚体的合成和化学物理表征，以及其与互补aegPNA的结合研究。我们通过CD和UV实验证明，l-dabPNA与aegPNA结合形成了具有良好热稳定性的复合物，我们将其鉴定为左手三元组。

  DOI：

  10.1016/j.bmcl.2008.08.005

文献信息

• [EN] MACROCYCLIC PEPTIDES USEFUL AS IMMUNOMODULATORS<br/>[FR] PEPTIDES MACROCYCLIQUES UTILES COMME IMMUNOMOLDULATEURS
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2016077518A1

  公开（公告）日：2016-05-19

  The present disclosure provides compounds which are immunomodulators and thus are useful for the amelioration of various diseases, including cancer and infectious diseases.

  本公开提供了一些免疫调节剂化合物，因此对于改善各种疾病，包括癌症和传染病，具有用处。
• Peptides and medical use thereof
  申请人：——

  公开号：US04997648A1

  公开（公告）日：1991-03-05

  Of therapeutic value in various contexts in which the cyclosporins are used, for example as anti-bacterial agents and particularly as immunosuppressive and anti-inflammatory agents, are acyclic undecapeptides having the formula (I) H--A.sub.1 --A.sub.2 --A.sub.3 --A.sub.4 --A.sub.5 --A.sub.6 --A.sub.7 --A.sub.8 --A.sub.9 --A.sub.10 --A.sub.11 --OH (I) in which A1 is either derived from 2-carboxyazetidine, 2-carboxypyrrolidine or 2-carboxypiperidine, which may optionally be substituted on a ring carbon atom other than that at position 2 by an amino, methylamino, mercapto or hydroxy group and/or by an acyclic aliphatic hydrocarbon group, or is an amino acid residue ##STR1## wherein n is 0, 1 or 2, X represents an amino, methylamino, mercapto or hydroxy group, R represents hydrogen or an acyclic aliphatic hydrocarbon group and R' represents hydrogen or a methyl group; A2 is an amino acid residue ##STR2## wherein R.sub.1 is an acyclic aliphatic hydrocarbon group, for example of 1 to 6 carbon atoms, optionally substituted at the C.sub.1 position of the group R.sub.1 by an amino, methylamino, mercapto or hydroxy group; A.sub.3 is a sarcosine residue; A.sub.4 is an N-methyl-leucine residue; A.sub.5 is a valine residue; A.sub.6 is an N-methyl-leucine residue; A.sub.7 is an alanine residue; A.sub.8 is an alanine residue; Ag is an N-methyl-leucine residue; A.sub.10 is an N-methyl-leucine or sarcosine residue; and A.sub.11 is an N-methylvaline residue; or such an acyclic undecapeptide in which one or more of the terminal amino or methylamino and carboxy groups and any amino, methylamino, mercapto or hydroxy group present in A.sub.1 or A.sub.2 is in derivative form.

  在环孢霉素用于抗菌剂、免疫抑制剂和抗炎剂等多种情境中具有治疗价值的无环十一肽具有公式（I）H--A.sub.1 --A.sub.2 --A.sub.3 --A.sub.4 --A.sub.5 --A.sub.6 --A.sub.7 --A.sub.8 --A.sub.9 --A.sub.10 --A.sub.11 --OH（I），其中A1可以是从2-羧基氮杂环丁烷、2-羧基吡咯烷或2-羧基哌啶衍生而来的，该环上的碳原子可以选择性地被氨基、甲基氨基、巯基或羟基取代，或者被无环脂肪烃基取代，或者是一个氨基酸残基##STR1##其中n为0、1或2，X代表氨基、甲基氨基、巯基或羟基，R代表氢或无环脂肪烃基，R'代表氢或甲基；A2是一个氨基酸残基##STR2##其中R.sub.1是一个无环脂肪烃基，例如1到6个碳原子，该基团的C.sub.1位置可以选择性地被氨基、甲基氨基、巯基或羟基取代；A.sub.3是一种肌氨酸残基；A.sub.4是一种N-甲基亮氨酸残基；A.sub.5是一种缬氨酸残基；A.sub.6是一种N-甲基亮氨酸残基；A.sub.7是一种丙氨酸残基；A.sub.8是一种丙氨酸残基；Ag是一种N-甲基亮氨酸残基；A.sub.10是一种N-甲基亮氨酸或肌氨酸残基；A.sub.11是一种N-甲基缬氨酸残基；或者这样一个无环十一肽，在其中，末端氨基或甲基氨基和羧基以及A.sub.1或A.sub.2中存在的任何氨基、甲基氨基、巯基或羟基均为衍生物形式。
• Cyclosporins
  申请人：——

  公开号：US05079341A1

  公开（公告）日：1992-01-07

  Cyclosporins having anti-bacterial activity useful as immuno suppressive and anti-inflammatory agents are provided, such as undecapeptides of the formula (I) ##STR1## in which A.sub.1 is either derived from 2-carboxyazetidine, 2-carboxypyrrolidine or 2-carboxypiperidine, or is an amino acid residue ##STR2## wherein n is 0, 1 or 2, X represents an amino, methylamino, mercapto or hydroxy group, R represents hydrogen or an acyclic aliphatic hydrocarbon group and R' represents hydrogen or methyl; A.sub.2 is an amino acid residue ##STR3## wherein R.sub.1 is an acyclic aliphatic hydrogen group optionally substituted at the C.sub.1 position of the group R.sub.1 by an amino, methylamino, mercapto or hydroxy group, but with the proviso that when R.sub.1 is a group of less than four carbon atoms then A.sub.1 is a heterocyclic amino acid residue or is an amino acid residue --R'N--CH(CHR(CH.sub.2).sub.n X)--CO-- wherein either (a) R is hydrogen or (b) R is an acyclic aliphatic hydrocarbon group and either n is O and X is an amino, methylamino or mercapto group, or n is 1 or 2 and X is an amino, methylamino, mercapto or hydroxy group; A.sub.3 is a sarcosine residue; A.sub.4 is an N-methyl-leucine residue; A.sub.5 is a valine residue; A.sub.6 is an M-methyl-leucine residue; A.sub.7 is an alanine residue; A.sub.8 is an alanine residue; A.sub.9 is an N-methyl-leucine residue; A.sub.10 is an N-methyl-leucine or sarcosine residue; and A.sub.11 is an N-methylvaline residue.

  本发明提供了具有抗菌活性的环孢霉素，可用作免疫抑制和抗炎剂，例如公式（I）的十一肽：##STR1## 其中A.sub.1从2-羧基氮杂环丙烷，2-羧基吡咯烷或2-羧基哌啶衍生，或者是氨基酸残基##STR2## 其中n为0、1或2，X表示氨基、甲基氨基、巯基或羟基，R表示氢或无环脂肪烃基，R'表示氢或甲基；A.sub.2是氨基酸残基##STR3## 其中R.sub.1是无环脂肪氢基团，可在R.sub.1的C.sub.1位置被氨基、甲基氨基、巯基或羟基取代，但是，当R.sub.1是少于四个碳原子的基团时，则A.sub.1是杂环氨基酸残基或者是氨基酸残基--R'N--CH(CHR(CH.sub.2).sub.n X)--CO--，其中（a）R为氢或（b）R为无环脂肪烃基，n为O且X为氨基、甲基氨基或巯基，或n为1或2且X为氨基、甲基氨基、巯基或羟基；A.sub.3是肌氨酸残基；A.sub.4是N-甲基亮氨酸残基；A.sub.5是缬氨酸残基；A.sub.6是M-甲基亮氨酸残基；A.sub.7是丙氨酸残基；A.sub.8是丙氨酸残基；A.sub.9是N-甲基亮氨酸残基；A.sub.10是N-甲基亮氨酸或肌氨酸残基；A.sub.11是N-甲基缬氨酸残基。
• Immunomodulators
  申请人：Bristol-Myers Squibb Company

  公开号：US20160137696A1

  公开（公告）日：2016-05-19

  The present disclosure provides compounds which are immunomodulators and thus are useful for the amelioration of various diseases, including cancer and infectious diseases.

  本公开提供具有免疫调节作用的化合物，因此可用于改善各种疾病，包括癌症和传染病。
• Synthesis and in vitro opioid activity profiles of DALDA analogues
  作者：Peter W Schiller、Thi M.-D Nguyen、Irena Berezowska、Sébastien Dupuis、Grazyna Weltrowska、Nga N Chung、Carole Lemieux

  DOI：10.1016/s0223-5234(00)01171-5

  日期：2000.10

  The tetrapeptide DALDA (H-Tyr-D-Arg-Phe-Lys-NH2) is a polar and selective mu agonist showing poor penetration of the placental and blood-brain barriers. In an effort to enhance the potency of DALDA, analogues containing 2',6'-dimethyltyrosine (Dmt), N,2',6'-trimethyltyrosine (Tmt), 2'-methyltyrosine (Mmt) or 2'-hydroxy,6'-methyltyrosine (Hmt) in place of Tyr(1), or Om or alpha,gamma -diaminobutyric acid (A(2)bu) in place of Lys(4), were synthesized. All compounds displayed high mu receptor selectivity in the rat and guinea pig brain membrane binding assays and most of them were more potent mu agonists than DALDA in the mu receptor-representative guinea pig ileum assay, with [Dmt(1)]DALDA showing the highest potency. Because of its extraordinary mu agonist potency, high mu selectivity, polar character (charge of 3+) and metabolic stability, [Dmt(1)]DALDA has potential for use in obstetrical or peripheral analgesia. (C) 2000 Editions scientifiques et medicales Elsevier SAS.