N-乙酰基-3-(3-吡啶基)-D-丙氨酸乙酯 | 103774-98-7

• 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
• 中文名称: N-乙酰基-3-(3-吡啶基)-D-丙氨酸乙酯
• 英文名称: N-acetyl-3-(3-pyridyl)-D-alanine ethyl ester
• 英文别名: ethyl (2R)-2-(acetylamino)-3-(3-pyridyl)propanoate；ethyl (2R)-2-acetamido-3-pyridin-3-ylpropanoate
• CAS: 103774-98-7
• 化学式: C₁₂H₁₆N₂O₃
• 分子量: 236.271
• InChiKey: UGVVAXGWDBKHRO-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  68.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-乙酰基-3-(3-吡啶基)-D-丙氨酸乙酯 、 盐酸 生成 3-(3-吡啶基)-D-丙氨酸
  参考文献：
  名称：

  NARASIMHA, RAO PEMMARAJU;BURDETT, J. E., JR.;CESSAC, J. W.;DINUNNO, C. M.+, INT. J. PEPTIDE AND PROTEIN RES., 29,(1987) N 1, 118-125

  摘要：

  DOI：
• 作为产物：
  描述：

  2-Acetamido-3-ethoxy-3-oxo-2-(pyridin-3-ylmethyl)propanoic acid 生成 N-乙酰基-3-(3-吡啶基)-D-丙氨酸乙酯
  参考文献：
  名称：

  NARASIMHA, RAO PEMMARAJU;BURDETT, J. E., JR.;CESSAC, J. W.;DINUNNO, C. M.+, INT. J. PEPTIDE AND PROTEIN RES., 29,(1987) N 1, 118-125

  摘要：

  DOI：
• 作为试剂：
  描述：

  N-acetyl-3-(3-pyridyl)-DL-alanine ethyl ester 、 水 、 氯化钾 、 氢氧化钾 在 乙酸乙酯 、 氯化钠 、 magnesium sulfate 、 N-乙酰基-3-(3-吡啶基)-D-丙氨酸乙酯 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 25.0~420.0 ℃ 、266.64 kPa 条件下， 反应 51.5h， 以are obtained in the form of a beige-colored solid melting at 80° C. [1H NMR spectrum (400 MHz, (CD3)2SO-d6, δ in ppm): 1.13 (t, J=7 Hz: 3H); 1.81 (s: 3H); 2.92 (dd, J=14 and 9.5 Hz: 1H); 3.05 (dd, J=14 and 5.5 Hz: 1H); 4.07 (q, J=7 Hz: 2H); 4.48 (mt: 1H); 7.33 (dd, J=8 and 5 Hz: 1H); 7.66 (dt, J=8 and 2 Hz: 1H); 8.36 (d, J=8 Hz: 1H); 8.44 (mt: 2H)]的产率得到N-乙酰基-3-(3-吡啶基)-D-丙氨酸乙酯
  参考文献：
  名称：

  Use of 2-aminothiazoline derivatives as inhibitors of inducible NO-synthase

  摘要：

  本发明涉及使用公式I中的2-氨基噻唑衍生物：1其中R1为氢原子或烷基基团，R2为烷基，-烷基-NH2，—CH2—R3，—CH2—S—R4或被硝基或—NH—C（═NH）CH3基团取代的苯基基团，或R1为烷基基团，R2为氢原子，R3为（3-6C）环烷基、吡啶基、吡啶N-氧化物、噻吩基、噻唑基、咪唑基、吡嗪基、三唑基或苯基基团或被硝基、羟基或羧基取代的苯基基团，R4表示吡啶基或吡啶N-氧化物基团，烷基表示烷基基团，或其药学上可接受的盐，作为诱导型NO合酶的抑制剂。

  公开号：

  US20020187987A1

文献信息

• 2-aminothiazoline derivatives and process for preparing the same
  申请人：——

  公开号：US20020198243A1

  公开（公告）日：2002-12-26

  The present invention relates to a class of 2-aminothiazoline derivatives of formula I: 1 in which either R 1 is a hydrogen atom or an alkyl radical and R 2 is an alkyl, -alk-NH 2 , —CH 2 —R 3 , —CH 2 —S—R 4 or phenyl radical substituted with a nitro or —NH—C(═NH)CH 3 radical, or R 1 is an alkyl radical and R 2 is a hydrogen atom, R 3 is a (3-6C) cycloalkyl, pyridyl, pyridyl N-oxide, thienyl, thiazolyl, imidazolyl, pyrazinyl, triazolyl or phenyl radical or a phenyl radical substituted with a nitro, hydroxy or carboxyl radical, R 4 represents a pyridyl or pyridyl N-oxide radical, alk represents an alkylene radical, or pharmaceutically acceptable salts thereof, which are useful as inhibitors of inducible NO-synthase.

  本发明涉及一类2-氨基噻唑啉衍生物，其化学式为I:1，其中R1为氢原子或烷基基团，R2为烷基、-烷基-NH2、—CH2—R3、—CH2—S—R4或取代有硝基或—NH—C(═NH)CH3基团的苯基基团，或R1为烷基基团，R2为氢原子，R3为(3-6C)环烷基、吡啶基、吡啶N-氧化物、噻吩基、噻唑基、咪唑基、吡嗪基、三唑基或苯基基团或取代有硝基、羟基或羧基的苯基基团，R4表示吡啶基或吡啶N-氧化物基团，alk表示烷基链，或其药学上可接受的盐，其作为诱导型NO合酶的抑制剂具有用途。
• Use of 2-aminothiazoline derivatives as inhibitors of inducible no-synthase
  申请人：——

  公开号：US20020022631A1

  公开（公告）日：2002-02-21

  The present invention relates to the use of 2-aminothiazoline derivatives of formula: 1 in which either R 1 is a hydrogen atom or an alkyl radical and R 2 is an alkyl, -alk-NH 2 , —CH 2 —R 3 , —CH 2 —S—R 4 or phenyl radical substituted with a nitro or —NH—C(═NH)CH 3 radical, or R 1 is an alkyl radical and R 2 is a hydrogen atom, R 3 is a (3-6C) cycloalkyl, pyridyl, pyridyl N-oxide, thienyl, thiazolyl, imidazolyl, pyrazinyl, triazolyl or phenyl radical or a phenyl radical substituted with a nitro, hydroxy or carboxyl radical, R 4 represents a pyridyl or pyridyl N-oxide radical, alk represents an alkylene radical, or pharmaceutically acceptable salts thereof, as inhibitors of inducible NO-synthase.

  本发明涉及使用式1中的2-氨基噻唑衍生物，其中R1为氢原子或烷基基团，R2为烷基，-烷基-NH2，-CH2-R3，-CH2-S-R4或苯基基团，其被硝基或-NH-C(═NH)CH3基团取代，或R1为烷基基团，R2为氢原子，R3为(3-6C)环烷基、吡啶基、吡啶N-氧化物、噻吩基、噻唑基、咪唑基、吡嗪基、三唑基或苯基基团或被硝基、羟基或羧基取代的苯基基团，R4代表吡啶或吡啶N-氧化物基团，alk代表烷基，或其药学上可接受的盐，作为可诱导型NO合酶的抑制剂。
• Chemoenzymatic routes to enantiomerically pure 2-azatyrosine and 2-, 3- and 4-pyridylalanine derivatives
  作者：Amer Moussa、Patrick Meffre、Jean Martinez、Valérie Rolland

  DOI：10.1007/s00726-010-0829-3

  日期：2012.4

  Enantiomerically pure 2-, 3- or 4-pyridylalanine (pya) and 2-azatyrosine (azatyr) are known to present various biological activities. After incorporation into appropriate peptide sequences, these heterocyclic non natural alpha-amino acids could behave as new substrates or inhibitors of elastase from Pseudomonas aeruginosa. This enzyme is known to be involved in nosocomial infections and infections related to the cystic fibrosis disease. New efficient chemoenzymatic preparations of those compounds using alpha-chymotrypsin (alpha-CT) are presented.
• New effective gonadotropin releasing hormone antagonists with minimal potency for histamine release in vitro
  作者：Jean E. Rivier、John Porter、Catherine L. Rivier、Marilyn Perrin、Anne Corrigan、William A. Hook、Reuben P. Siraganian、Wylie W. Vale

  DOI：10.1021/jm00160a008

  日期：1986.10

  In order to minimize the adverse effect of histamine release in the rat of some gonadotropin releasing hormone (GnRH) antagonists, such as [Ac-D2Nal1,D4FPhe2,DTrp3,DArg6]-GnRH, new structures with modifications at positions 1, 2, 3, 5, 6, 7, and 10 were synthesized and tested in several biological systems. In vitro: the affinity for the pituitary GnRH receptor was measured as was the ability of the analogues to inhibit GnRH-stimulated release of luteinizing hormone (LH) by dispersed anterior pituitary cells in culture and to release histamine from rat mast cells. In vivo: inhibition of ovulation in the cycling rat was determined after subcutaneous (sc) injection of the peptides at noon on the day of proestrus; the duration of action of the peptides was evaluated by measuring LH levels in the castrated male rat after sc injection of some selected analogues. [Ac-D2Nal1,D4ClPhe2,D3Pal3,Arg5,D-4-p-methoxy benzoyl-2-aminobutyric acid6,DAla10]-GnRH was found to be one of the most potent analogues of this series, causing a 100% inhibition of ovulation at 5 micrograms/kg or less. Release of histamine was observed at doses 10-25 times that required for [Ac-D2Nal1,D4FPhe2,DTrp3,DArg6]-GnRH. Thus, introduction of arginine in position 5 with a hydrophobic amino acid in position 6 is compatible with high potency in several biological systems and results in compounds with lowered potency to release histamine compared to homologous peptides with tyrosine in position 5 and D-arginine in position 6.
• NARASIMHA, RAO PEMMARAJU;BURDETT, J. E., JR.;CESSAC, J. W.;DINUNNO, C. M.+, INT. J. PEPTIDE AND PROTEIN RES., 29,(1987) N 1, 118-125
  作者：NARASIMHA, RAO PEMMARAJU、BURDETT, J. E., JR.、CESSAC, J. W.、DINUNNO, C. M.+

  DOI：——

  日期：——