(S)-2-amino-N-methyl-3-(naphthalen-2-yl)propanamide | 142880-44-2

• 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: (S)-2-amino-N-methyl-3-(naphthalen-2-yl)propanamide
• 英文别名: (S)-2-naphthylalanine-N-methylamide；2-(S)-amino-N-methyl-3-naphthalen-2-yl-propionamide；L-3-(2-naphthyl)alanine N-methylamide；L-3-(2-naphthyl)-alanine methylamide；(2S)-2-amino-N-methyl-3-naphthalen-2-ylpropanamide
• CAS: 142880-44-2
• 化学式: C₁₄H₁₆N₂O
• 分子量: 228.294
• InChiKey: PCVUKAGITSGGQA-ZDUSSCGKSA-N

物化性质

• 沸点：
  475.7±38.0 °C(Predicted)
• 密度：
  1.145±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-amino-N-methyl-3-(naphthalen-2-yl)propanamide 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 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、294.18 kPa 条件下， 生成 (2R)-N'-hydroxy-N-[(2S)-1-(methylamino)-3-naphthalen-2-yl-1-oxopropan-2-yl]-2-(2-methylpropyl)butanediamide
  参考文献：
  名称：

  Synthesis and biological evaluation of orally active matrix metalloproteinase inhibitors

  摘要：

  The synthesis and biological evaluation of orally active inhibitors of matrix metalloproteinase are reported. Modifications of the P2' position and the a-substituent of hydroxamic acid derivatives were carried out, and revealed that the P2' substituent influenced the MMP inhibitory activities in vitro and in plasma after oral administration. The hydroxamates with phenylglycine at the P2' position were absorbed well orally. Compound 15e, which exhibited the longest duration of inhibitory activity in plasma after oral administration among the phenylglycine derivatives (5a-5d, 15a, 15c, 15e), was evaluated in a rat adjuvant arthritis model. A reduction in hind foot pad swelling and improvements of some inflammatory parameters were demonstrated when the compound was administered orally. These results indicate the potential of MMP inhibitors for rheumatoid arthritis. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00028-x
• 作为产物：
  描述：

  Boc-3-(2-萘基)-L-丙氨酸 在 氯甲酸乙酯 、 三乙胺 、 三氟乙酸 作用下， 反应 3.5h， 生成 (S)-2-amino-N-methyl-3-(naphthalen-2-yl)propanamide
  参考文献：
  名称：

  Synthesis and biological evaluation of orally active matrix metalloproteinase inhibitors

  摘要：

  The synthesis and biological evaluation of orally active inhibitors of matrix metalloproteinase are reported. Modifications of the P2' position and the a-substituent of hydroxamic acid derivatives were carried out, and revealed that the P2' substituent influenced the MMP inhibitory activities in vitro and in plasma after oral administration. The hydroxamates with phenylglycine at the P2' position were absorbed well orally. Compound 15e, which exhibited the longest duration of inhibitory activity in plasma after oral administration among the phenylglycine derivatives (5a-5d, 15a, 15c, 15e), was evaluated in a rat adjuvant arthritis model. A reduction in hind foot pad swelling and improvements of some inflammatory parameters were demonstrated when the compound was administered orally. These results indicate the potential of MMP inhibitors for rheumatoid arthritis. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00028-x

文献信息

• Substituted Dihydroisoquinolinones by Iodide-Promoted Cyclocarbonylation of Aromatic α-Amino Acids
  作者：Mostafa M. Amer、Ana C. Carrasco、Daniel J. Leonard、John W. Ward、Jonathan Clayden

  DOI：10.1021/acs.orglett.8b03551

  日期：2018.12.21

  of aromatic α-amino acids, on treatment with phosgene and potassium iodide, undergo a mild Bischler–Napieralski-style cyclocarbonylation reaction that generates a tricyclic lactam by insertion of a C═O group between amino acid nitrogen and the ortho position of the aryl substituent. Regio- and diastereoselective functionalization of the lactam generates a library of substituted dihydroisoquinolinones

  一系列芳香族 α-氨基酸的咪唑啉酮衍生物在用光气和碘化钾处理后，会发生温和的 Bischler-Napieralski 式环羰基化反应，通过在氨基酸氮和邻位之间插入 C=O 基团生成三环内酰胺。芳基取代基的位置。内酰胺的区域选择性和非对映选择性功能化产生了取代的二氢异喹啉酮及其对映体富集形式的同源物库。
• Diazacycloalkanedione derivatives
  申请人：——

  公开号：US20020061878A1

  公开（公告）日：2002-05-23

  Compounds of formula I 1 wherein R is carboxy, esterified carboxy or amidated carboxy; R 1 and R 3 are independently lower alkyl, (hydroxy, lower alkoxy, amino, acylamino, mono- or di-lower alkylamino or mercapto)-lower alkyl, lower alkyl-(thio, sulfinyl or sulfonyl)-lower alkyl, cycloalkyl, aryl, biaryl, (cycloalkyl, aryl or biaryl)-lower alkyl, or (carboxy, esterified carboxy or amidated carboxy)-lower alkyl; R 2 is hydrogen, lower alkyl, cycloalkyl, aryl, biaryl, arylaminocarbonyl, or aryl-(oxy, thio or amino); n is 1 or 2; Y is lower-alkylene or lower alkenylene; and pharmaceutically acceptable salts thereof; which are useful as LFA-1 antagonists.

  式I1的化合物，其中R是羧基，酯化羧基或酰胺化羧基；R1和R3独立地是较低的烷基，（羟基，较低的烷氧基，氨基，酰胺基，单或双较低的烷氨基或巯基）-较低的烷基，较低的烷基-(硫醚基，亚砜基或砜基)-较低的烷基，环烷基，芳基，联苯基，（环烷基，芳基或联苯基）-较低的烷基，或（羧基，酯化羧基或酰胺化羧基）-较低的烷基；R2是氢，较低的烷基，环烷基，芳基，联苯基，芳基氨基甲酰基，或芳基-(氧基，硫基或氨基)；n为1或2；Y为较低的烷基或较低的烯基；及其药学上可接受的盐；这些化合物作为LFA-1拮抗剂是有用的。
• Melanocortin receptor ligands
  申请人：Ebetino Hallock Frank

  公开号：US20060128613A1

  公开（公告）日：2006-06-15

  Disclosed are MC-4 and/or MC-3 receptor ligands, the ligands having a structure according to Formula (I): wherein R 2 , R 4 , R 4′ , R 5 , R 6 , R 6′ , R 7 , R 8 , R 8′ , R 9 , R 9′ , R 10 , Ar, Z 1 , Z 2 , Z 3 , X, B, D, p, q, r and s are as described in the specification and claims, and optical isomers, diastereomers or enantiomers thereof; pharmaceutically-acceptable salts, hydrates, and biohydrolyzable esters, amides or imides thereof. Also disclosed are pharmaceutical compositions comprising the ligands of Formula (I), as well as methods of treating diseases mediate by the MC-4/MC-3 receptors, as described in the Detailed Descriptions section of the specification.

  公开了MC-4和/或MC-3受体配体，该配体具有按照式（I）的结构：其中R2、R4、R4'、R5、R6、R6'、R7、R8、R8'、R9、R9'、R10、Ar、Z1、Z2、Z3、X、B、D、p、q、r和s如说明书和索赔中所述，以及其光学异构体、二对映异构体或对映体；药用盐、水合物和生物水解酯、酰胺或亚酰胺。还公开了包括式（I）配体的药物组合物，以及治疗由MC-4/MC-3受体介导的疾病的方法，如说明书的详细描述部分所述。
• A useful synthesis of the Phe-Arg phosphinic acid dipeptide isostere
  作者：Andrew S Kende、Han-Qing Dong、Xuewei Liu、Frank H Ebetino

  DOI：10.1016/s0040-4039(02)00957-7

  日期：2002.7

  A modular method for construction of polypeptides containing the Phe-Arg phosphinic acid isostere is described.

  描述了构建含有Phe-Arg次膦次膦酸等排物的多肽的模块化方法。
• Compounds For the Inhibition of Undesired Cell Proliferation and Use Thereof
  申请人：Knolle Jochen

  公开号：US20080194524A1

  公开（公告）日：2008-08-14

  The present invention is related to compounds having formula (I) wherein the dashed line indicates a single or double bond or is absent and wherein A 1 -A 9 , Q, R 1 -R 11 , T, U, V, W 1 -W 3 , X 1 , X 2 , Y and Z are as defined in the claims and description, pharmaceutical compositions comprising the compounds and the use of the compounds for the manufacture of a medicament for the treatment of diseases involving abnormal cell proliferation, undesired cell proliferation, abnormal mitosis and/or undesired mitosis.

  本发明涉及具有式（I）的化合物，其中虚线表示单键或双键或不存在，A1-A9，Q，R1-R11，T，U，V，W1-W3，X1，X2，Y和Z如权利要求和说明书所定义，包括该化合物的制药组合物和用于制造治疗涉及异常细胞增殖、不良细胞增殖、异常有丝分裂和/或不良有丝分裂疾病药物的化合物的用途。