phenylmethyl N2-{[(1,1-dimethylethyl)oxy]carbonyl}-N1-methyl-L-α-asparaginate | 57499-33-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: phenylmethyl N2-{[(1,1-dimethylethyl)oxy]carbonyl}-N1-methyl-L-α-asparaginate
• 英文别名: N-tert-butoxycarbonyl-L-aspartic acid 1-methylamide 4-benzyl ester；Boc-Asp(OBzl)-NHMe；benzyl (3S)-4-(methylamino)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoate
• CAS: 57499-33-9
• 化学式: C₁₇H₂₄N₂O₅
• 分子量: 336.388
• InChiKey: HFOLVDYMTHSVOB-ZDUSSCGKSA-N

物化性质

• 沸点：
  542.4±50.0 °C(Predicted)
• 密度：
  1.148±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  phenylmethyl N2-{[(1,1-dimethylethyl)oxy]carbonyl}-N1-methyl-L-α-asparaginate 在 盐酸 、 4 A molecular sieve 、 silver trifluoromethanesulfonate 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 、 1,1,3,3-四甲基脲 、 tin(ll) chloride 作用下， 以 1,4-二氧六环 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 39.5h， 生成 -L-aspartic acid 1-methylamide 5-benzyl ester
  参考文献：
  名称：

  Studies on Selectin Blockers. 7. Structure−Activity Relationships of Sialyl Lewis X Mimetics Based on Modified Ser-Glu Dipeptides

  摘要：

  We have previously found that heterochiral fucodipeptides, L-Ser-D-Glu (3a) and D-Ser-L-Glu (3b), exhibited up to 20-100 times more potency than a sialyl Lewis X (sLe(x), 1) and a 3'-sulfated Lewis X analogue (2) toward E-selectin binding and have also proposed, from molecular dynamics calculation, that their strong activities would depend on a possible formation of the type II and/or type II' beta-turn of compounds 3a,b (Tsukida, T.; Hiramatsu, Y.; Tsujishita, H.; Kiyoi, T.; Yoshida, M.; Kurokawa, K.; Moriyama, H.; Ohmoto, H.; Wada, Y.; Saito, T.; Kondo, H. J. Med. Chem. 1997, 40, 3534-3541). To clarify our hypothesis, we synthesized several analogues of compounds 3a,b and investigated their structure-activity relationships. As a result, it was indicated that the type II and/or type II' beta-turn conformation would be a comparatively tight form and would play important roles in favorable binding to E-selectin. These findings indicate that sLe(x) mimetics with type II and type II'-beta-turn dipeptides could be a useful methodology for the design of an active selectin blocker.

  DOI：

  10.1021/jm980267x
• 作为产物：
  描述：

  Boc-L-天冬氨酸 4-苄酯 、 盐酸甲胺 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 异丁酰胺 为溶剂， 反应 18.0h， 以78%的产率得到phenylmethyl N2-{[(1,1-dimethylethyl)oxy]carbonyl}-N1-methyl-L-α-asparaginate
  参考文献：
  名称：

  PYRROLIDINONE ANILINES AS PROGESTERONE RECEPTOR MODULATORS

  摘要：

  本发明涉及以下公式所代表的化合物：或其药用可接受盐，或其溶剂化合物，或其组合物，其中R1、R2和X如本文所定义。本发明的化合物可用作孕激素受体调节剂。

  公开号：

  US20080039517A1

文献信息

• Fucose derivatives, drugs containing the same as active ingredient, and
  申请人：Kanebo, Ltd

  公开号：US05919769A1

  公开（公告）日：1999-07-06

  A compound of the formula (I): ##STR1## wherein X.sup.1 is a group of one of the following formulae (1), (2) and (3): ##STR2## R.sup.1 is a branched long chain alkyl group, R.sup.2 is --CONHR.sup.3, a carboxyl group or a hydrogen atom, n is an integer of 0, 1 or 2, and R.sup.3 is a lower alkyl group or a phenyl group, or a pharmaceutically acceptable salt thereof, which is useful as a selectin inhibitor, and can be used in the prophylaxis or treatment of various inflammatory diseases such as inflammatory dermatitis (e.g., atopic dermatitis, contact hypersensitivity, photodermatosis, etc.), autoimmune chronic diseases (e.g. rheumatoid arthritis, chronic thyroiditis, etc.), and ischemia-reperfusion injury.

  化合物的公式（I）：##STR1##其中X.sup.1是以下公式之一的基团（1）、（2）和（3）：##STR2##R.sup.1是支链长链烷基基团，R.sup.2是--CONHR.sup.3、羧基或氢原子，n是0、1或2的整数，R.sup.3是较低的烷基基团或苯基，或其药学上可接受的盐，用作选择素抑制剂，可用于预防或治疗各种炎症性疾病，如炎症性皮炎（例如特应性皮炎、接触性过敏、光敏性皮炎等）、自身免疫慢性疾病（例如类风湿关节炎、慢性甲状腺炎等）和缺血再灌注损伤。
• Amino acid derivatives and application thereof
  申请人：Fuji Photo Film Co., Ltd.

  公开号：US05763408A1

  公开（公告）日：1998-06-09

  There are disclosed amino acid derivatives represented by the following general formula (I): ##STR1## wherein L.sup.1 and L.sup.2 represent an amino acid residue etc., A.sup.1 and A.sup.3 represent C.dbd.O, A.sup.2 represents an alkylene group etc., m and n represent an integer of 1 to 5, V represents --NHC(.dbd.NH)NH.sub.2 etc., W represents --COOH etc., R.sup.1 and R.sup.2 represent hydrogen atom, alkyl group etc., R.sup.3 and R.sup.4 represent hydrogen etc. and X and Y represent --NH-- or --O-- and pharmaceutically acceptable salts thereof and agents for inhibiting tumor matastasis containing the compounds, and the amino acid derivatives exhibit high activity for inhibiting tumor metastasis and weak platelet aggregation inhibition activity and weak anticoagulation activity.

  以下是一般公式（I）所代表的氨基酸衍生物：##STR1## 其中 L.sup.1 和 L.sup.2 代表氨基酸残基等，A.sup.1 和 A.sup.3 代表 C.dbd.O，A.sup.2 代表烷基等，m 和 n 代表 1 到 5 的整数，V 代表 --NHC(.dbd.NH)NH.sub.2 等，W 代表 --COOH 等，R.sup.1 和 R.sup.2 代表氢原子，烷基等，R.sup.3 和 R.sup.4 代表氢等，X 和 Y 代表 --NH-- 或 --O--，以及其药学上可接受的盐和抑制肿瘤转移的药物，该氨基酸衍生物表现出高抑制肿瘤转移活性和弱血小板聚集抑制活性和弱抗凝活性。
• Pyrrolidinone anilines as progesterone receptor modulators
  申请人：GlaxoSmithKline LLC

  公开号：US07816395B2

  公开（公告）日：2010-10-19

  The present invention relates to a compound represented by the following formula: or a pharmaceutically acceptable salt thereof, or a solvate thereof, or a combination thereof, wherein R1, R2, and X are as defined herein. Compounds of the present invention are useful as progesterone receptor modulators.

  本发明涉及下列式子所代表的化合物：或其药学上可接受的盐、溶剂化物或其组合物，其中R1、R2和X的定义如本文所述。本发明的化合物可用作孕激素受体调节剂。
• FUCOSE DERIVATIVES, DRUGS CONTAINING THE SAME AS ACTIVE INGREDIENT, AND INTERMEDIATES FOR PRODUCING THE SAME
  申请人：KANEBO, LTD.

  公开号：EP0859005A1

  公开（公告）日：1998-08-19

  A compound of the formula (I): wherein X1 is a group of one of the following formulae (1), (2) and (3): R1 is a branched long chain alkyl group, R2 is ―CONHR3, a carboxyl group or a hydrogen atom, n is an integer of 0, 1 or 2, and R3 is a lower alkyl group or a phenyl group, or a pharmaceutically acceptable salt thereof, which is useful as a selectin inhibitor, and can be used in the prophylaxis or treatment of various inflammatory diseases such as inflammatory dermatitis (e.g., atopic dermatitis, contact hypersensitivity, photodermatosis, etc.), autoimmune chronic diseases (e.g. rheumatoid arthritis, chronic thyroiditis, etc.), and ischemia-reperfusion injury.

  式 (I) 的化合物： 其中 X1 是下式（1）、（2）和（3）之一的基团： R1是支链长链烷基，R2是-CONHR3、羧基或氢原子，n是0、1或2的整数，R3是低级烷基或苯基，或其药学上可接受的盐，可作为选择素抑制剂，用于预防或治疗各种炎症性疾病，如炎症性皮炎（如、特应性皮炎、接触性过敏、光敏性皮肤病等）、自身免疫性慢性疾病（如类风湿性关节炎、慢性甲状腺炎等）以及缺血再灌注损伤。
• US5919769A
  申请人：——

  公开号：US5919769A

  公开（公告）日：1999-07-06