ethyl L-tryptophanylglycinate | 67865-62-7

• 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: ethyl L-tryptophanylglycinate
• 英文别名: [(2S)-amino-3-(1H-indol-3-yl)-propionylamino]-acetic acid ethyl ester；ethyl L-tryptophylglycinate；ethyl 2-[[(2S)-2-amino-3-(1H-indol-3-yl)propanoyl]amino]acetate
• CAS: 67865-62-7
• 化学式: C₁₅H₁₉N₃O₃
• 分子量: 289.334
• InChiKey: RUNBFMGGGCJIDL-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  97.2
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl L-tryptophanylglycinate 在 4-二甲氨基吡啶 、 sodium hydroxide 、 三丁基膦 、 一水合肼 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 31.0h， 生成 (4S)-4-(3-indolylmethyl)-1,2,3,4-tetrahydro-5H-pyrazino[2,1-b]quinazoline-3,6-dione
  参考文献：
  名称：

  A New Route toward 4-Substituted Pyrazino[2,1-b]quinazoline-3,6-dione Systems. Total Synthesis of Glyantrypine

  摘要：

  Treatment of sodium N-(o-azidobenzoyl)aminoacylglycinates 8 with acetic anhydride afforded 1-acetyl-4-(o-azidobenzoyl)-2,5-piperazinediones 7, with complete retention of the stereochemistry. The intramolecular aza Wittig reactions of compounds 7 in the presence of tributylphosphine followed by deacetylation gave 1,2-unsubstituted pyrazino[2,1-b]quinazoline-3,6-diones 1. This route was adapted to the synthesis of both enantiomers of the alkaloid glyantrypine.

  DOI：

  10.1021/jo991626e
• 作为产物：
  描述：

  N-苄氧羰基-L-色氨酸 在 palladium on activated charcoal 氢气 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 32.0h， 生成 ethyl L-tryptophanylglycinate
  参考文献：
  名称：

  A New Route toward 4-Substituted Pyrazino[2,1-b]quinazoline-3,6-dione Systems. Total Synthesis of Glyantrypine

  摘要：

  Treatment of sodium N-(o-azidobenzoyl)aminoacylglycinates 8 with acetic anhydride afforded 1-acetyl-4-(o-azidobenzoyl)-2,5-piperazinediones 7, with complete retention of the stereochemistry. The intramolecular aza Wittig reactions of compounds 7 in the presence of tributylphosphine followed by deacetylation gave 1,2-unsubstituted pyrazino[2,1-b]quinazoline-3,6-diones 1. This route was adapted to the synthesis of both enantiomers of the alkaloid glyantrypine.

  DOI：

  10.1021/jo991626e

文献信息

• [EN] 2-PHENOXY- AND 2-PHENYLSULFOMAMIDE DERIVATIVES WITH CCR3 ANTAGONISTIC ACTIVITY FOR THE TREATMENT OF ASTHMA AND OTHER INFLAMMATORY OR IMMUNOLOGICAL DISORDERS<br/>[FR] DERIVES DE 2-PHENOXY- ET 2-PHENYLSULFONAMIDE A ACTIVITE ANTAGONISTE DE CCR3 POUR LE TRAITEMENT DE L'ASTHME ET D'AUTRES TROUBLES INFLAMMATOIRES OU IMMUNOLOGIQUES
  申请人：BAYER HEALTHCARE AG

  公开号：WO2004084898A1

  公开（公告）日：2004-10-07

  The present invention relates to a benzenesulfonamide derivative of formula (I), which is useful as an active ingredient of pharmaceutical preparations. The benzenesulfonamide derivatives of the present invention have CCR3 (CC type chemokine receptor) antagonistic activity, and can be used for the prophylaxis and treatment of diseases associated with CCR3 activity, in particular for the treatment of asthma, atopic dermatitis, allergic rhinitis and other inflammatory/immunological disorders. In said formula, X represents O or S; R4 represents formulae (a), (b), (c), (d), (e), (f), (g), (h), (i) or (j), the other substituents are as defined in claim 1.

  该发明涉及一种公式(I)的苯磺酰胺衍生物，可用作药物制剂的活性成分。该发明的苯磺酰胺衍生物具有CCR3（CC型趋化因子受体）拮抗活性，可用于预防和治疗与CCR3活性相关的疾病，特别是用于治疗哮喘、特应性皮炎、过敏性鼻炎和其他炎症/免疫性疾病。在上述公式中，X代表O或S；R4代表公式(a)、(b)、(c)、(d)、(e)、(f)、(g)、(h)、(i)或(j)，其他取代基如权利要求书中所定义。
• 2-Phenoxy- and 2-phenylsulfomamide derivatives with ccr3 antagonistic activity for the treatment of asthma and other inflammatory or immunological disorders
  申请人：Li Yingfu

  公开号：US20070155725A1

  公开（公告）日：2007-07-05

  The present invention relates to a benzenesulfonamide derivative of formula (I), which is useful as an active ingredient of pharmaceutical preparations. The benzenesulfonamide derivatives of the present invention have CCR3 (CC type chemokine receptor) antagonistic activity, and can be used for the prophylaxis and treatment of diseases associated with CCR3 activity, in particular for the treatment of asthma, atopic dermatitis, allergic rhinitis and other inflammatory/immunological disorders. In said formula, X represents O or S; R 4 represents formulae (a), (b), (c), (d), (e), (f), (g), (h), (i) or (j), the other substituents are as defined in claim 1.

  本发明涉及一种苯磺酰胺衍生物，其化学式为(I)，可用作制药制剂的活性成分。本发明的苯磺酰胺衍生物具有CCR3（CC型趋化因子受体）拮抗活性，可用于预防和治疗与CCR3活性相关的疾病，特别是用于哮喘、特应性皮炎、过敏性鼻炎和其他炎症/免疫性疾病的治疗。在上述化学式中，X代表O或S；R4代表式(a)、(b)、(c)、(d)、(e)、(f)、(g)、(h)、(i)或(j)，其他取代基如权利要求书所定义。
• 2-Phenoxy- and 2-Phenylsulfonamide Derivatives with CCR3 Antagonistic Activity for the Treatment of Inflammatory or Immunological Disorders
  申请人：Li Yingfu

  公开号：US20090286771A1

  公开（公告）日：2009-11-19

  Provided herein are 2-phenoxy- and 2-phenylsulfonamide derivatives with CCR3 antagonistic activity. These compounds are useful for the treatment of diseases associated with CCR3 activity, including but not limited to, atopic dermatitis, allergic rhinitis, rheumatoid arthritis, Grave's disease, HIV infection, Alzheimer's disease, atherosclerosis and other inflammatory and/or immunological disorders.

  在此提供具有CCR3拮抗活性的2-苯氧基和2-苯基磺酰胺衍生物。这些化合物可用于治疗与CCR3活性相关的疾病，包括但不限于特应性皮炎、过敏性鼻炎、类风湿性关节炎、格雷夫病、HIV感染、阿尔茨海默病、动脉粥样硬化和其他炎症和/或免疫性疾病。
• 2-phenoxy- and 2-phenylsulfanyl-benzenesulfonamide derivatives with ccr3 antagonistic activity for the treatment of asthma and other inflammatory or immunological disorders
  申请人：Actimis Pharmaceuticals, Inc.,

  公开号：EP1997495A1

  公开（公告）日：2008-12-03

  The present invention relates to a benzenesulfonamide derivative of formula (I), which is useful as an active ingredient of pharmaceutical preparations. The benzenesulfonamide derivatives of the present invention have CCR3 (CC type chemokine receptor) antagonistic activity, and can be used for the prophylaxis and treatment of disease associated with CCR3 activity, in particular for the treatment of asthma, atopic dermatitis, allergic rhinitis and other inflammatory/immunological disorders. wherein X represents O or S; R4 represents the other substituents are as defined in claim 1.

  本发明涉及一种式（I）的苯磺酰胺衍生物，可用作药物制剂的活性成分。本发明的苯磺酰胺衍生物具有 CCR3（CC 型趋化因子受体）拮抗活性，可用于预防和治疗与 CCR3 活性相关的疾病，特别是用于治疗哮喘、特应性皮炎、过敏性鼻炎和其他炎症/免疫性疾病。 其中 X 代表 O 或 S R4 代表 其他取代基如权利要求 1 所定义。
• 2-PHENOXY- AND 2-PHENYLSULFOMAMIDE DERIVATIVES WITH CCR3 ANTAGONISTIC ACTIVITY FOR THE TREATMENT OF ASTHMA AND OTHER INFLAMMATORY OR IMMUNOLOGICAL DISORDERS
  申请人：Actimis Pharmaceuticals, Inc.

  公开号：EP1608374B1

  公开（公告）日：2008-11-05