N-benzyloxycarbonyl-N-isobutylglycine | 189031-00-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-benzyloxycarbonyl-N-isobutylglycine
• 英文别名: n-((Benzyloxy)carbonyl)-n-isobutylglycine；2-[2-methylpropyl(phenylmethoxycarbonyl)amino]acetic acid
• CAS: 189031-00-3
• 化学式: C₁₄H₁₉NO₄
• 分子量: 265.309
• InChiKey: QDOIGLFBFMDSMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-benzyloxycarbonyl-N-isobutylglycine 在 乙酸酐 、 乙酰氯 作用下， 反应 6.0h， 以70%的产率得到3-isobutyl-oxazolidine-2,5-dione
  参考文献：
  名称：

  Polypeptoids from N-Substituted Glycine N-Carboxyanhydrides: Hydrophilic, Hydrophobic, and Amphiphilic Polymers with Poisson Distribution

  摘要：

  Preparation of defined and functional polymers has been one of the hottest topics in polymer science and drug delivery in the recent decade. Also, research on (bio)degradable polymers gains more and more interest, in particular at the interface of these two disciplines. However, in the majority of cases, combination of definition, functionality and degradability, is problematic. Here we present the preparation and characterization (MALDI-ToF MS, NMR, GPC) of nonionic hydrophilic, hydrophobic, and amphiphilic N-substituted polyglycines (polypeptoids), which are expected to be main-chain degradable and are able to disperse a hydrophobic model compound in aqueous media. Polymerization kinetics suggest that the polymerization is well controlled with strictly linear pseudo first-order kinetic plots to high monomer consumption. Moreover, molar mass distributions of products are Poisson-type and molar mass can be controlled by the monomer to initiator ratio. The presented polymer platform is nonionic, backbone degradable, and synthetically highly flexible and may therefore be valuable for a broad range of applications, in particular as a biomaterial.

  DOI：

  10.1021/ma201015y
• 作为产物：
  描述：

  在 lithium hydroxide monohydrate 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 生成 N-benzyloxycarbonyl-N-isobutylglycine
  参考文献：
  名称：

  无添加剂水基介质中更环保的拟肽合成

  摘要：

  为更绿色地合成序列定义的拟肽低聚物开发了高效程序。优化的链伸长过程在水基介质中以独特的N到C方向进行，包括方便的一锅两步脱保护/耦合序列，用于安装每个新的 peptoid 残基。该过程非常高效，每个中间偶联步骤后唯一需要的后处理程序是水萃取。与传统程序形成鲜明对比的是，在合成和后处理过程中，除水外，唯一使用的溶剂是 EtOH、MeOH 或 EtOAc。此外，除了反应介质中的试剂外，不需要专门的水溶性保护基团或添加剂。

  DOI：

  10.1039/d3gc00400g

文献信息

• Inhibitors of cysteine protease
  申请人：SmithKline Beecham corporation

  公开号：US20020128476A1

  公开（公告）日：2002-09-12

  This invention relates to compounds of formula (I): 1 wherein: A is C(O) or CH(OH); R 1 is 2 R 2 is H, C 1-6 alkyl, C 3-6 cycloalkyl-C 0-6 alkyl, Ar-C 0-6 alkyl, Het-C 0-6 alkyl, R 5 C(O)—, R 5 C(S)—, R 5 S0 2 —, R 5 OC(O)—, R 5 R′NC(O)—, R 5 R′NC(S)—, adamantyl-C(O)—, or 3 R″ is H, C 1-6 alkyl, Ar-C 0-6 alkyl, or Het-C 0-6 alkyl; R′″ is H, C 1-6 alkyl, C 3-6 cycloalkyl-C 0-6 alkyl, Ar-C 0-6 alkyl, or Het-C 0-6 alkyl;

  本发明涉及式(I)的化合物： 其中： A为C(O)或CH(OH)； R1为2； R2为H、C1-6烷基、C3-6环烷基-C0-6烷基、Ar-C0-6烷基、Het-C0-6烷基、R5C(O)、R5C(S)、R5S02、R5OC(O)、R5R′NC(O)、R5R′NC(S)、adamantyl-C(O)或3； R″为H、C1-6烷基、Ar-C0-6烷基或Het-C0-6烷基； R′″为H、C1-6烷基、C3-6环烷基-C0-6烷基、Ar-C0-6烷基或Het-C0-6烷基。
• INHIBITORS OF CYSTEINE PROTEASE
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP0936912A1

  公开（公告）日：1999-08-25
• EP0936912A4
  申请人：——

  公开号：EP0936912A4

  公开（公告）日：1999-10-13
• [EN] INHIBITORS OF CYSTEINE PROTEASE<br/>[FR] INHIBITEURS DE LA PROTEASE A CYSTEINE
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：WO1998005336A1

  公开（公告）日：1998-02-12

  (EN) This invention relates to compounds of formula (I), wherein A is C(O) or CH(OH); R1 is (1), (2), (3) or (4); R2 is H, C1-6alkyl, C3-6cycloalkyl-C0-6alkyl, Ar-C0-6alkyl, Het-C0-6alkyl, R5C(O)-, R5C(S)-, R5SO2-, R5OC(O)-, R5R'NC(O)-, R5R'NC(S)-, adamantyl-C(O)-, or (5); R' is H, C1-6alkyl, Ar-C0-6alkyl, or Het-C0-6alkyl; R'' is H, C1-6alkyl, C3-6cycloalkyl-C0-6alkyl, Ar-C0-6alkyl, or Het-C0-6alkyl; each R3 independently is H, C2-6alkenyl, C2-6alkynyl, Het, Ar or C1-6alkyl optionally substituted by OR', SR', NR'2, R'NC(O)OR5, CO2R', CO2NR'2, N(C=NH)NH2, Het or Ar; R4 is H, C1-6alkyl, C3-6cycloalkyl-C0-6alkyl, Ar-C0-6alkyl, Het-C0-6alkyl, R5C(O)-, R5C(S)-, R5SO2-, R5OC(O)-, R5R'NC(O)-, R5R'NC(S)-, R'HNCH(R')C(O)-, or R5OC(O)NR'CH(R')C(O)-; each R5 independently is C3-6cycloalkyl-C0-6alkyl, Ar-C0-6alkyl, Het-C0-6alkyl, Ar-C0-6alkoxy, Het-C0-6alkoxy, or C1-6alkyl optionally substituted by OR', SR', NR'2, R'NC(O)OR5, CO2R', CO2NR'2, N(C=NH)NH2, Het or Ar; R6 is H, C1-6alkyl, Ar-C0-6alkyl, or Het-C0-6alkyl and R7 is H, C1-6alkyl, C3-6cycloalkyl-C0-6alkyl, Ar-C0-6alkyl, Het-C0-6alkyl, R5C(O)-, R5C(S)-, R5SO2-, R5OC(O)-, R5R'NC(O)-, R5R'NC(S)-, R'HNCH(R')C(O)-, or R5OC(O)NR'CH(R')C(O)-; or R6 and R7 are connected to form a pyrrolidine, a piperidine, or a morpholine ring; each R' independently is H, C1-6alkyl, Ar-C0-6alkyl, or Het-C0-6alkyl; R* is H, C1-6alkyl, C3-6cycloalkyl-C0-6alkyl, Ar-C0-6alkyl, or Het-C0-6alkyl; Y is a single bond or O; each Z independently is CO or CH2; and n is 0, 1, or 2; or a pharmaceutically acceptable salt thereof, which are inhibitors of cysteine proteases, particularly cathepsin K, and are useful in the treatment of diseases in which inhibition of bone loss is a factor.(FR) L'invention porte sur des composés de formule (I) dans laquelle: A est C(O) ou CH(OH); R1 est (1), (2), (3) ou (4), R2 est H, C1-6alkyl, C3-6cycloalkyl-C0-6alkyl, Ar-C0-6alkyl, Het-C0-6alkyl, R5C(O)-, R5SO2-, R5OC(O)-, R5R'NC(O)-, R5R'NC(S)-, adamantyl-C(O)-, ou (5); R' est H, C1-6alkyl, Ar-C0-6alkyl, ou Het-C0-6alkyl; R'' est H, C1-6alkyl, C3-6cycloalkyl-C0-6alkyl, Ar-C0-6alkyl, ou Het-C0-6alkyl; chaque R3 est indépendamment H, C2-6alcényl, C2-6alcynyl, Het, Ar ou C1-6alkyl facultativement substitué par OR', SR', NR'2, R'NC(O)OR5, CO2R', CO2NR'2, N(C=NH)NH2, Het ou Ar; R4 est H, C1-6alkyl, C3-6cycloalkyl-C0-6alkyl, Ar-C0-6alkyl, Het-C0-6alkyl, R5C(O)-, R5C(S)-, R5SO2-, R5OC(O)-, R5R'NC(O)-, R5R'NC(S)-, R'HNCH(R')C(O)-, ou R5OC(O)NR'CH(R')C(O)-; chaque R5 est indépendamment C3-6cycloalkyl-C0-6alkyl, Ar-C0-6alkyl, Het-C0-6alkyl, Ar-C0-6alkoxy, Het-C0-6alkoxy, ou C1-6alkyl facultativement substitué par OR', SR', NR'2, R'NC(O)OR5, CO2R', CO2NR'2, NC(C=NH)NH2, Het ou Ar; R6 est H, C1-6alkyl, Ar-C0-6alkyl, ou Het-C0-6alkyl et R7 est H, C1-6alkyl, C3-6cycloalkyl-C0-6alkyl, Ar-C0-6alkyl, Het-C0-6alkyl, R5C(O)-, R5C(S)-, R5SO2-, R5-OC(O)-, R5R'NC(O)-, R5R'NC(S)-, R'HNCH(R')C(O)-, ou R5OC(O)NR'CH(R')C(O)-; ou R6 et R7 sont liés pour constituer un cycle pyrrolidine, pipéridine ou morpholine; chaque R' est indépendamment H, C1-6alkyl, Ar-C0-6alkyl, ou Het-C0-6alkyl; R* est H, C1-6alkyl, C3-6cycloalkyl-C0-6alkyl, Ar-C0-6alkyl, ou Het-C0-6alkyl; Y est une liaison simple ou O; chaque Z est indépendamment CO ou CH2; et n est 0, 1 or 2; ou leurs sels pharmacocompatibles qui sont des inhibiteurs de la protéase à cystéine et en particulier de la cathépsine K et servent au traitement de maladies dans lesquelles l'inhibition de la déperdition osseuse joue un rôle.
• Polypeptoids from <i>N</i>-Substituted Glycine <i>N</i>-Carboxyanhydrides: Hydrophilic, Hydrophobic, and Amphiphilic Polymers with Poisson Distribution
  作者：Corinna Fetsch、Arlett Grossmann、Lisa Holz、Jonas F. Nawroth、Robert Luxenhofer

  DOI：10.1021/ma201015y

  日期：2011.9.13

  Preparation of defined and functional polymers has been one of the hottest topics in polymer science and drug delivery in the recent decade. Also, research on (bio)degradable polymers gains more and more interest, in particular at the interface of these two disciplines. However, in the majority of cases, combination of definition, functionality and degradability, is problematic. Here we present the preparation and characterization (MALDI-ToF MS, NMR, GPC) of nonionic hydrophilic, hydrophobic, and amphiphilic N-substituted polyglycines (polypeptoids), which are expected to be main-chain degradable and are able to disperse a hydrophobic model compound in aqueous media. Polymerization kinetics suggest that the polymerization is well controlled with strictly linear pseudo first-order kinetic plots to high monomer consumption. Moreover, molar mass distributions of products are Poisson-type and molar mass can be controlled by the monomer to initiator ratio. The presented polymer platform is nonionic, backbone degradable, and synthetically highly flexible and may therefore be valuable for a broad range of applications, in particular as a biomaterial.