IGly(N^α-Cbz)-OH | 158831-35-7

• 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: IGly(N^α-Cbz)-OH
• 英文别名: N-carboxybenzyl-N-isopropylaminoacetic acid；N-(benzyloxycarbonyl)-N-isopropylglycine；2-{[(Benzyloxy)carbonyl](propan-2-yl)amino}acetic acid；2-[phenylmethoxycarbonyl(propan-2-yl)amino]acetic acid
• CAS: 158831-35-7
• 化学式: C₁₃H₁₇NO₄
• 分子量: 251.282
• InChiKey: OBQBASXGBGUANM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  IGly(N^α-Cbz)-OH 在 乙酸酐 、 乙酰氯 作用下， 反应 5.0h， 以72%的产率得到3-isopropyloxazolidine-2,5-dione
  参考文献：
  名称：

  Thermoresponsive Poly(N-C3 glycine)s

  摘要：

  Ring-opening polymerization of N-substituted glycine N-carboxyanhydrides (NCAs) was applied to prepare a series of well-defined poly(N-C3 glycine)s (C3 = n-propyl, allyl, propargyl, and isopropyl), polypeptoids, with molecular weights in the range of 1.8-6.6 kg mol(-1). Poly(N-isopropyl glycine), a previously unreported poly-peptoid, could be obtained by bulk polymerization of the corresponding NCA in the melt. The samples were characterized by spectroscopy (NMR and FT-IR), size exclusion chromatography (SEC), and matrix-assisted laser desorption/ionization time-of-flight mass spectroscopy (MALDI-ToF MS). The polymers could be dispersed in water up to 20-40 g L-1; the poly(N-propargyl glycine) was not soluble in water. Turbidity measurements of the three water-soluble polypeptoids illustrated cloud point temperatures dependent on structural and electronic properties of the side chain. The cloud point temperatures were found to increase in the order C3 = n-propyl (15-25 degrees C) < allyl (27-54 degrees C) < isopropyl (47-58 degrees C). Long-term annealing of the aqueous solution of poly(N-{n-propyl} glycine) and poly(N-allyl glycine) above the cloud point temperature resulted in the formation of crystalline microparticles with melting points of 188-198 and 157-165 degrees C (differential scanning calorimetry, DSC), respectively, and rose bud type morphology (scanning electron microscopy, SEM).

  DOI：

  10.1021/ma302412v
• 作为产物：
  描述：

  N-异丙基甘氨酸盐酸盐 、 氯甲酸苄酯 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 4.25h， 以95%的产率得到IGly(N^α-Cbz)-OH
  参考文献：
  名称：

  Thermoresponsive Poly(N-C3 glycine)s

  摘要：

  Ring-opening polymerization of N-substituted glycine N-carboxyanhydrides (NCAs) was applied to prepare a series of well-defined poly(N-C3 glycine)s (C3 = n-propyl, allyl, propargyl, and isopropyl), polypeptoids, with molecular weights in the range of 1.8-6.6 kg mol(-1). Poly(N-isopropyl glycine), a previously unreported poly-peptoid, could be obtained by bulk polymerization of the corresponding NCA in the melt. The samples were characterized by spectroscopy (NMR and FT-IR), size exclusion chromatography (SEC), and matrix-assisted laser desorption/ionization time-of-flight mass spectroscopy (MALDI-ToF MS). The polymers could be dispersed in water up to 20-40 g L-1; the poly(N-propargyl glycine) was not soluble in water. Turbidity measurements of the three water-soluble polypeptoids illustrated cloud point temperatures dependent on structural and electronic properties of the side chain. The cloud point temperatures were found to increase in the order C3 = n-propyl (15-25 degrees C) < allyl (27-54 degrees C) < isopropyl (47-58 degrees C). Long-term annealing of the aqueous solution of poly(N-{n-propyl} glycine) and poly(N-allyl glycine) above the cloud point temperature resulted in the formation of crystalline microparticles with melting points of 188-198 and 157-165 degrees C (differential scanning calorimetry, DSC), respectively, and rose bud type morphology (scanning electron microscopy, SEM).

  DOI：

  10.1021/ma302412v

文献信息

• Iterative Approach to the Discovery of Novel Degarelix Analogues:  Substitutions at Positions 3, 7, and 8. Part II
  作者：Manoj P. Samant、Jozsef Gulyas、Doley J. Hong、Glenn Croston、Catherine Rivier、Jean Rivier

  DOI：10.1021/jm050134t

  日期：2005.7.1

  extent (efficacy and duration of action) of inhibition of luteinizing hormone (LH) release. Structurally, this series of analogues has novel substitutions at positions 3, 7, and 8 and N(alpha)-methylation at positions 6, 7, and 8 in the structure of degarelix. These substitutions were designed to probe the spatial limitations of the receptor's cavity and to map the steric and ionic boundaries. Some

  Degarelix（FE200486，Ac-d-2Nal（1）-d-4Cpa（2）-d-3Pal（3）-Ser（4）-4Aph（1-Hor）（5）-d-4Aph（Cbm）（6 ）-Leu（7）-ILys（8）-Pro（9）-d-Ala（10）-NH（2））是哺乳动物皮下给药后促性腺激素释放激素（GnRH）的强效且长效拮抗剂包括人类。在表达人GnRH受体的HEK-293细胞中，通过报告基因分析法合成，表征并表征了地加瑞克的类似物，并筛选了GnRH诱导的应答的拮抗作用。在去势雄性大鼠试验中还测定了作用的持续时间，以测量抑制黄体生成素（LH）释放的程度（作用和作用的持续时间）。从结构上讲，这一系列类似物在地加瑞克的结构中的3、7和8位具有新的取代基，并在6、7和8位具有Nα-甲基化。设计这些替代物以探测受体腔的空间限制并绘制空间和离子边界。引入了一些官能团，这些官能团被认为会影响类似物的药动学性
• NOVEL COMPOUNDS FOR USE AS HIV PROTEASE INHIBITORS
  申请人：F.HOFFMANN-LA ROCHE AG

  公开号：EP1339692A1

  公开（公告）日：2003-09-03
• US6472404B1
  申请人：——

  公开号：US6472404B1

  公开（公告）日：2002-10-29
• [EN] NOVEL COMPOUNDS FOR USE AS HIV PROTEASE INHIBITORS<br/>[FR] NOUVEAUX COMPOSANTS SERVANT D'INHIBITEURS DE PROTEASE VIH
  申请人：HOFFMANN LA ROCHE

  公开号：WO2002042277A1

  公开（公告）日：2002-05-30

  Disclosed are compounds of general formula (I) and pharmaceutically acceptable salts thereof wherein R1 is H, hydroxy or NHR2 wherein R2 is H, alkyl, alkenyl, alkynyl, arylalkyl, heterocyclyalkyl, cycloalkyl, alkyl carbonyl, cycloalkyl carbonyl, aryl carbonyl, heterocyclyl carbonyl, aryl alkyl carbonyl, heterocyclyl alkyl carbonyl, alkyl oxy carbonyl, aryl alkyl oxy carbonyl, heterocyclyl alkyl oxy carbonyl, aryl heterocyclyl sulfonyl, alkyl sulfonyl, aryl sulfonyl, heterocyclyl sulfonyl or a group of formula (A) wherein X is O or S and R?7 and R8¿ independently are H, alkyl, aryl, heterocyclyl, aryl alkyl, heterocyclyl alkyl or R7 an R8 together with the notrogen atom to which they are attached form a saturated ring optionally containing a further hetero atom or a group (B) wherein when n=1, Y represents N, R9 is H or alkyl and R10 H, alkyl, aryl, alkyl, heterocyclyl alkyl, aryl, heterocyclyl or R?9 and R10¿ taken together with the hetero atom to which they are attached form a heterocycle R?11 and R12¿ independently are H or alkyl or R?11 and R12¿ taken together with the carbon atom to which they are attached form a cycle, R3, R4 independently are alkyl or taken together with the carbon atom to which they are attached form a carbocycle, R5 is alkyl, aryl alkyl, heterocyclyl alkyl or R?4 and R5¿ taken together with the carbon and sulfur atom to which they are attached form a heterocycle and R6 is alkyl, aryl alkyl, heterocyclyl alkyl, alkyl oxy alkyl, hydroxy alkyl, amino alkyl, fluoro alkyl and R13 is H or the residue of an inorganic ester and R15 is aryl, with the proviso that, if R?3, R4 and R5¿ are methyl, R6 is tert.butyl, R13 is H and if R15 is phenyl R2 is not benzyl oxycarbonyl and not 2-quinoline carbonyl. The compounds of formula (I) are potent inhibitors of the HIV aspartyl protease and can therefore be used in the treatment of HIV related diseases.