N-tetrahydrofurfurylaminoacetic acid ethyl ester | 41681-92-9

• 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: N-tetrahydrofurfurylaminoacetic acid ethyl ester
• 英文别名: Ethyl 2-[(oxolan-2-ylmethyl)amino]acetate；ethyl 2-(oxolan-2-ylmethylamino)acetate
• CAS: 41681-92-9
• 化学式: C₉H₁₇NO₃
• mdl: MFCD01159116
• 分子量: 187.239
• InChiKey: OHJSXMVSFDTZAT-UHFFFAOYSA-N

物化性质

• 沸点：
  266.0±15.0 °C(Predicted)
• 密度：
  1.045±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.888
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-tetrahydrofurfurylaminoacetic acid ethyl ester 在 sodium methylate 、 碳酸氢钠 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 22.0h， 生成 methyl 4-(pyrrolidin-2-yl)-7-((tetrahydrofuran-2-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylate
  参考文献：
  名称：

  Synthesis of 7-alkyl-4-amino-7H-pyrrolo-[2,3-d]pyrimidine-6-carboxylic acids

  摘要：

  Two variants are discussed for the synthesis of ethyl N-alkyl-N-(6-amino-5-formylpyrimidin-4-yl)-glycinate derivatives, which are converted by intramolecular cyclization under the influence of sodium methoxide to give methyl 7H-pyrrolo[2,3-d]pyrimidine-6-carboxylates. New derivatives of pyrimido- [5',4':4,5]pyrrolo[2,1-c][1,4]oxazines containing 3-chloropropyl groups at position 8 have been prepared.

  DOI：

  10.1007/s10593-013-1218-0

文献信息

• Thrombin inhibitors. 3. Carboxyl-containing amide derivatives of N.alpha.-substituted L-arginine
  作者：Ryoji Kikumoto、Yoshikuni Tamao、Kazuo Ohkubo、Tohru Tezuka、Shinji Tonomura、Shosuke Okamoto、Akiko Hijikata

  DOI：10.1021/jm00186a003

  日期：1980.12

  N alpha-(arylsulfonyl)-L-arginine amide derivatives having carboxamide N-substituents with a carboxyl group was prepared and tested as inhibitors of the clotting activity of thrombin. The most inhibitory compounds were obtained when a carboxyl group was introduced into the carbon next to the amide nitrogen of N alpha-(arylsulfonyl)-L-arginine amide derivatives, e.g., N alpha-(arylsulfonyl)-L-arginyl-N-butyl-

  制备了一系列具有羧基羧基酰胺N-取代基的Nα-（芳基磺酰基）-L-精氨酸酰胺衍生物，并测试了它们作为凝血酶凝血活性的抑制剂。当在Nα-（芳基磺酰基）-L-精氨酸酰胺衍生物（例如Nα-（芳基磺酰基）-L-精氨酸-N-丁基）的酰胺氮旁的碳原子中引入羧基时，获得最具抑制性的化合物。 -，N-（甲氧基乙基）-或N-（四氢糠基）甘氨酸和4-烷基-1- [Nα-（芳基磺酰基）-L-精氨酰基] -2-哌啶甲酸，I50为1-3 X 10（ -7）M.
• Inhibition of human leukocyte elastase (HLE) by N-substituted peptidyl trifluoromethyl ketones
  作者：Jerry W. Skiles、Victor Fuchs、Clara Miao、Ronald Sorcek、Karl G. Grozinger、Scott C. Mauldin、Jana Vitous、Philip W. Mui、Stephen Jacober

  DOI：10.1021/jm00082a005

  日期：1992.2

  A series of tripeptides possessing trifluoromethyl or aryl ketone residues at P1 were prepared and evaluated both in vitro and in vivo as potential inhibitors of human leukocyte elastase (HLE). Tripeptides containing non naturally occurring N-substituted glycine residues at the P2-position have been demonstrated to be potent in vitro inhibitors of HLE, with IC50 values in the submicromolar range. Sterically demanding substituents on the P2-nitrogen have no detrimental effect on in vitro potency. The inhibition process presumably acts via hemiketal formation with the active site Ser195 of HLE, and is facilitated by the strongly electron withdrawing trifluoromethyl functionality. Deletion of the amino acid at the P3-subsite region affords inactive compounds. Valine is the preferred residue at the P1-position, whereas the corresponding glycine, alanine, alpha,alpha-dimethylglycine, or phenylalanine analogues are all inactive. The compounds described herein all confer a high degree of in vitro specificity when tested against representative cysteine, aspartyl, metallo, and other serine proteases. One of the most potent in vitro inhibitors is (3RS)-N-[4-[[[(4-chlorophenyl)sulfonyl]amino]carbonyl]phenyl]oxomethyl]-L-valyl-N-(2,3-dihydro-1H-inden-2-yl)glycine N-[3-(1,1,1-trifluoro-4-methyl-2-oxopentyl)]amide (20i; BI-RA-260) (IC50 = 0.084-mu-M). Compound 20i was also tested in hamsters in an elastase-induced pulmonary hemorrhage (EPH) model. In this model, intratracheal (it.) administration of 20i, 5 min prior to HLE challenge, effectively inhibited hemorrhage in a dose-dependent manner with an ED50 of 4.8-mu-g. The inhibitor 20i, 20-mu-g administered it. 24, 48, and 72 h prior to HLE challenge, exhibits significant inhibition against hemorrhage at all time points (97%, 64% and 49%, respectively). In a 21-day chronic model of emphysema in hamsters, 200-mu-g of HLE administered it. caused an elastase-induced emphysema in the lungs which can be quantitated histologically utilizing image analysis. In this assay, 20i significantly inhibited pulmonary lesions associated with septal destruction and increased alveolar spaces, when dosed at 20-mu-g it. 5 min prior to challenge with HLE.
• Convenient approach to the synthesis of pyrimido[5',4':4,5]pyrrolo[2,4-c][1,4]oxazine, a new heterocyclic system
  作者：O. B. Smolii、L. V. Muzychka、E. V. Verves

  DOI：10.1007/s10593-010-0423-3

  日期：2009.10
• US4140681A
  申请人：——

  公开号：US4140681A

  公开（公告）日：1979-02-20
• Synthesis of 7-alkyl-4-amino-7H-pyrrolo-[2,3-d]pyrimidine-6-carboxylic acids
  作者：E. V. Verves、A. V. Kucher、L. V. Muzychka、O. B. Smolii

  DOI：10.1007/s10593-013-1218-0

  日期：2013.3

  Two variants are discussed for the synthesis of ethyl N-alkyl-N-(6-amino-5-formylpyrimidin-4-yl)-glycinate derivatives, which are converted by intramolecular cyclization under the influence of sodium methoxide to give methyl 7H-pyrrolo[2,3-d]pyrimidine-6-carboxylates. New derivatives of pyrimido- [5',4':4,5]pyrrolo[2,1-c][1,4]oxazines containing 3-chloropropyl groups at position 8 have been prepared.