(S)-tryptophan N-methyl amide hydrochloride

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (S)-tryptophan N-methyl amide hydrochloride
• 英文别名: hydrochloride salt of L-tryptophan methylamide；(2S)-2-amino-3-(1H-indol-3-yl)-N-methylpropanamide;hydrochloride
• 化学式: C₁₂H₁₅N₃O*ClH
• 分子量: 253.732
• InChiKey: FRHNUELNJPGPEO-PPHPATTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.21
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  70.9
• 氢给体数：
  4
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-tryptophan N-methyl amide hydrochloride 在 氢氧化钾 、 盐酸羟胺 、 三乙胺 、 N,N'-羰基二咪唑 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 伊洛马司他
  参考文献：
  名称：

  Matrix Metalloproteinase Inhibitors:  A Structure−Activity Study

  摘要：

  Modifications around the dipeptide-mimetic core of a hydroxamic acid based matrix metalloproteinase inhibitor were studied. These variations incorporated a variety of natural, unnatural, and synthetic amino acids in addition to modifications of the P1' and P3' substituents. The results of this study indicate the following structural requirements: (1) Two key hydrogen bonds must be present between the enzyme and potent substrates. (2) Potent inhibitors must possess strong zinc-binding functionalities. (3) The potential importance of the hydrophobic group at position R3 as illustrated by its ability to impart greater relative potency against stromelysin when larger hydrophobic groups are used. (4) Requirements surrounding the nature of the amino acid appear to be more restrictive for stromelysin than for neutrophil collagenase, 72 kDa gelatinase, and 92 kDa gelatinase. These requirements may involve planar fused-ring aryl systems and possibly hydrogen-bonding capabilities.

  DOI：

  10.1021/jm970494j
• 作为产物：
  描述：

  N-叔丁氧羰基-L-色氨酸 在 盐酸 、 N,N-Diisopropylethylamine p-toluenesulfonate salt 、 1-丙基磷酸酐 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 4.0h， 生成 (S)-tryptophan N-methyl amide hydrochloride
  参考文献：
  名称：

  一种萘啶酰胺类化合物及其制备方法与应用

  摘要：

  本发明公开了一种萘啶酰胺类化合物及其制备方法与应用，该萘啶酰胺类化合物具有式(A)的结构或其农药学上可接受的盐或其光学异构体； 本发明萘啶酰胺类化合物作为促分裂原活化蛋白激酶Mps1抑制剂，表现出优良的抑制稻瘟菌等真菌致病能力，可以有效防治水稻稻瘟病等真菌病害。

  公开号：

  CN115043834A

文献信息

• Process for preparing synthetic matrix metalloprotease inhibitors
  申请人：Glycomed Incorporated

  公开号：US05892112A1

  公开（公告）日：1999-04-06

  Synthetic mammalian matrix metalloprotease inhibitors are disclosed that are useful for treating or preventing diseases wherein said diseases are caused by unwanted mammalian matrix metalloprotease activity and include skin disorders, keratoconus, restenosis, rheumatoid arthritis, wounds, cancer, angiogenesis and shock.

  揭示了一种合成的哺乳动物基质金属蛋白酶抑制剂，用于治疗或预防由不需要的哺乳动物基质金属蛋白酶活性引起的疾病，包括皮肤疾病、角膜圆锥症、再狭窄、类风湿关节炎、伤口、癌症、血管生成和休克。
• Highly Enantioselective Diels–Alder Reaction Catalyzed by Chiral Imidazolidinone
  作者：Yongjiang Wang、Xiaoliang Xu、Wen Pei

  DOI：10.1080/00397910802632571

  日期：2009.5.7

  Abstract New chiral imidazolidinone with an indole group was synthesized and used to catalyze the Diels–Alder reaction of α,β-unsaturated aldehyde with diene. High enantiomeric excesses and good yields were obtained. The reaction media were also surveyed. The best result in terms of enantioselectivity was achieved using acrolein and 2,3-dimethylbutdiene (up to 95% ee) in CH3OH/H2O.

  摘要 合成了具有吲哚基团的新型手性咪唑烷酮，用于催化α,β-不饱和醛与二烯的Diels-Alder反应。获得了高对映体过量和良好的产率。还调查了反应介质。在 CH3OH/H2O 中使用丙烯醛和 2,3-二甲基丁二烯（高达 95% ee）实现了对映选择性方面的最佳结果。
• Inhibition of angiogenesis by synthetic matrix metalloprotease inhibitors
  申请人：——

  公开号：US05268384A1

  公开（公告）日：1993-12-07

  Synthetic mammalian matrix metalloprotease inhibitors are useful in controlling angiogenesis. These compounds are thus useful in controlling the growth of tumors and in controlling neovascular glaucomas.

  合成哺乳动物基质金属蛋白酶抑制剂在控制血管生成方面非常有用。因此，这些化合物对于控制肿瘤的生长和控制新生血管性青光眼非常有用。
• Matrix metalloprotease inhibitors
  申请人：——

  公开号：US05189178A1

  公开（公告）日：1993-02-23

  Compounds of the formulas ##STR1## wherein each R.sup.1 is independently H or alkyl (1-8C) and R.sup.2 is alkyl (1-8C) or wherein the proximal R.sup.1 and R.sup.2 taken together are --(CH.sub.2).sub.p -- wherein p=3-5; R.sup.3 is H or alkyl (1-4C); R.sup.4 is fused or conjugated unsubstituted or substituted bicycloaryl methylene; n is 0, 1 or 2; m is 0 or 1; and X is OR.sup.5 or NHR.sup.5, wherein R.sup.5 is H or substituted or unsubstituted alkyl (1-12C), aryl (6-12C), aryl alkyl (6-16C); or X is an amino acid residue or amide thereof; or X is the residue of a cyclic amine or heterocyclic amine; wherein R.sup.6 is H or lower alkyl (1-4C) and R.sup.7 is H, lower alkyl (1-4C) or an acyl group, and wherein --CONR.sup.3 -- is optionally in modified isosteric form are useful for treating conditions which are characterized by unwanted matrix metalloprotease activities.

  化合物的结构式为##STR1##，其中每个R.sup.1独立地为H或烷基（1-8C），R.sup.2为烷基（1-8C），或者接近的R.sup.1和R.sup.2共同为--(CH.sub.2).sub.p --，其中p=3-5；R.sup.3为H或烷基（1-4C）；R.sup.4为融合或共轭的未取代或取代的双环芳基亚甲基；n为0、1或2；m为0或1；X为OR.sup.5或NHR.sup.5，其中R.sup.5为H或取代或未取代的烷基（1-12C）、芳基（6-12C）、芳基烷基（6-16C）；或X为氨基酸残基或其酰胺；或X为环胺或杂环胺的残基；其中R.sup.6为H或较低烷基（1-4C），R.sup.7为H、较低烷基（1-4C）或酰基，以及--CONR.sup.3 --可以选择以修改的同工异构形式存在，用于治疗其特征为不需要的基质金属蛋白酶活性的病况。
• Treatment for tissue ulceration
  申请人：University of Florida

  公开号：US05114953A1

  公开（公告）日：1992-05-19

  Compounds of the formulas ##STR1## wherein R.sup.1 is H and R.sup.2 is alkyl (3-8C) or wherein R.sup.1 and R.sup.2 taken together are --(CH.sub.2).sub.n -- wherein n=3-5; R.sup.3 is H or alkyl (1-4C); R.sup.4 is a substituted or unsubstituted fused or conjugated bicycloaryl methylene; X is OR.sup.5 or NHR.sup.5, wherein R.sup.5 is H or substituted or unsubstituted alkyl (1-12C), aryl (6-12C), aryl alkyl (6-16C); or X is an amino acid residue or amide thereof; or X is the residue of a cyclic amine or heterocyclic amine are useful for treating or preventing ulceration of tissue, especially cornea.

  这些化合物的化学式为##STR1##其中R.sup.1为H，R.sup.2为烷基(3-8C)，或者R.sup.1和R.sup.2一起为--(CH.sub.2).sub.n--，其中n=3-5；R.sup.3为H或烷基(1-4C)；R.sup.4为取代或未取代的融合或共轭的双环芳基亚甲基；X为OR.sup.5或NHR.sup.5，其中R.sup.5为H或取代或未取代的烷基(1-12C)、芳基(6-12C)、芳基烷基(6-16C)；或者X为氨基酸残基或其酰胺；或者X为环胺或杂环胺的残基，可用于治疗或预防组织溃疡，尤其是角膜溃疡。