tert-butyl (S)-(1-amino-3-(3-fluorophenyl)-1-oxopropan-2-yl)carbamate | 119744-84-2

• 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: tert-butyl (S)-(1-amino-3-(3-fluorophenyl)-1-oxopropan-2-yl)carbamate
• 英文别名: tert-butyl N-[(2S)-1-amino-3-(3-fluorophenyl)-1-oxopropan-2-yl]carbamate
• CAS: 119744-84-2
• 化学式: C₁₄H₁₉FN₂O₃
• 分子量: 282.315
• InChiKey: XEKZQIPDOJQZHP-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  81.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (S)-(1-amino-3-(3-fluorophenyl)-1-oxopropan-2-yl)carbamate 在 盐酸 、 碳酸氢钠 、 1-羟基苯并三唑 、 溶剂黄146 、 苯甲醚 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.0h， 生成 ({[(S)-1-Carbamoyl-2-(3-fluoro-phenyl)-ethyl]-ethyl-carbamoyl}-methyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Peripherally acting enkephalin analogs. 2. Polar tri- and tetrapeptides

  摘要：

  The design, synthesis, and biological activity of a series of D-Arg2-enkephalin-derived tetrapeptide amides and tripeptide aralkylamides are reported. These polar analogues were designed to be excluded from the central nervous system with their action thus limited to peripheral opioid receptors. The effects of the nature of the aromatic ring, aryl ring substitution, and aralkylamine chain length on activity were investigated; in a number of cases the N-terminal amino group of Tyr1 was converted to a guanidino group to further increase hydrophilicity. The peptides were all synthesized by classical solution methodology. The opioid activity of the peptides was assessed in vitro on the guinea pig ileum and their antinociceptive activity was determined in vivo in chemically induced writhing models (peripheral activity) and in the hot-plate test (central activity), in rodents. That the analgesic effects were predominantly mediated in the periphery was demonstrated by antagonism of antinociception by the peripheral opioid antagonist N-methylnalorphine and by comparison of the activities in the writhing and hot-plate tests. As a class, the tetrapeptides were more potent than the tripeptides; N alpha-amidination generally increased activity. A number of compounds exhibited very potent opioid activity and had the desired pharmacological profile, indicating a high degree of peripheral selectivity.

  DOI：

  10.1021/jm00125a028
• 作为产物：
  描述：

  BOC-L-3-氟苯丙氨酸 在 N,N'-羰基二咪唑 、 氨 作用下， 以 氯仿 、 四氢呋喃 为溶剂， 反应 1.67h， 以100%的产率得到tert-butyl (S)-(1-amino-3-(3-fluorophenyl)-1-oxopropan-2-yl)carbamate
  参考文献：
  名称：

  WO2008/85505

  摘要：

  公开号：

文献信息

• Opioid receptor modulators and products and methods related thereto
  申请人：Epiodyne, Inc.

  公开号：US11352316B2

  公开（公告）日：2022-06-07

  Compounds are provided having the structure of Formula (I): or a pharmaceutically acceptable isomer, racemate, hydrate, solvate, isotope, or salt thereof, wherein A, B, L, R3, R4, R5, R6, R8, m and n are as defined herein. Such compounds modulate the opioid receptor, particulare the mu-opioid receptor (MOR) and/or the kappa-opioid receptor (KOR), and/or the delta-opioid receptor (DOR). Products containing such compounds, as well as methods for their use and preparation, are also provided.

  所提供的化合物具有式 (I) 结构： 或其药学上可接受的异构体、外消旋体、水合物、溶液、同位素或盐，其中 A、B、L、R3、R4、R5、R6、R8、m 和 n 如本文所定义。此类化合物可调节阿片受体，尤其是μ阿片受体（MOR）和/或卡巴阿片受体（KOR）和/或δ阿片受体（DOR）。此外，还提供了含有此类化合物的产品及其使用和制备方法。
• WO2019195634A5
  申请人：——

  公开号：WO2019195634A5

  公开（公告）日：2022-04-11
• Highly Potent Cyclic Disulfide Antagonists of Somatostatin
  作者：Simon J. Hocart、Rahul Jain、William A. Murphy、John E. Taylor、David H. Coy

  DOI：10.1021/jm9806289

  日期：1999.6.1

  The search for synthetic analogues of somatostatin (SRIF) which exhibit selective affinities for the five known receptor subtypes (sst(1-5)) has generated a large number of potent agonist analogues. Many of these agonists display good subtype selectivities and affinities for the subtypes 2, 3, and 5, with very few selective for sst(1) or sst(4). Until the recent report by Bass and co-workers (Mol. Pharmacol. 1996, 50, 709-715; erratum Mel. Pharmacol. 1997, 51, 170), no true antagonists of somatostatin had been discovered, let alone any displaying differential receptor subtype selectivity. In this present study, we further explore the effect of this putative L,D-5(6) antagonist motif on somatostatin octapeptide analogues with a cyclic hexapeptide core. The most potent antagonist found to date is H-Cpa-cyclo[DCys-Tyr-DTrp-Lys-Thr-Cys]-Nal-NH2, PRL-2970 (21), which has an IC50 Of 1.1 nM in a rat pituitary growth hormone in vitro antagonist assay versus SRIF (1 nM). This analogue bound to cloned human somatostatin subtype 2 receptors with a K-i of 26 nM. The highest hsst(2) affinity analogue was H-Cpa-cyclo[DCys-Pal-DTrp-Lys-Tle-Cys]-Nal-NH2, PRL-2915 (15), with a K-i of 12 nM (IC50 = 1.8 nM). This analogue was also selective for hsst(2) over hsst(3) and hsst(5) by factors of 8 and 40, respectively, and had no agonist activity when tested alone at concentrations up to 10 mu M. Regression analysis of the binding affinities versus the observed antagonist potencies revealed high correlations for hsst(2) (r = 0.65) and hsst(3) (r = 0.52) with a less significant correlation to hsst5 (r = 0.40). This is quite different from the somatostatin agonist analogues which show a highly significant correlation to hsst(2) (r > 0.9). Receptor-selective somatostatin antagonists should provide valuable tools for characterizing the many important physiological functions of this neuropeptide.
• OPIOID RECEPTOR MODULATORS AND PRODUCTS AND METHODS RELATED THERETO
  申请人：Epiodyne, Inc.

  公开号：US20210147343A1

  公开（公告）日：2021-05-20

  Compounds are provided having the structure of Formula (I): or a pharmaceutically acceptable isomer, racemate, hydrate, solvate, isotope, or salt thereof, wherein A, B, L, R 3 , R 4 , R 5 , R 6 , R 8 , m and n are as defined herein. Such compounds modulate the opioid receptor, particulate the mu-opioid receptor (MOR) and/or the kappa-opioid receptor (KOR), and/or the delta-opioid receptor (DOR). Products containing such compounds, as well as methods for their use and preparation, are also provided.
• [EN] OPIOID RECEPTOR MODULATORS AND PRODUCTS AND METHODS RELATED THERETO<br/>[FR] MODULATEURS DU RÉCEPTEUR OPIOÏDE, PRODUITS ET PROCÉDÉS ASSOCIÉS
  申请人：EPIODYNE INC

  公开号：WO2019195634A1

  公开（公告）日：2019-10-10

  Compounds are provided having the structure of Formula (I): or a pharmaceutically acceptable isomer, racemate, hydrate, solvate, isotope, or salt thereof, wherein A, B, L, R3, R4, R5, R6, R8, m and n are as defined herein. Such compounds modulate the opioid receptor, particulare the mu-opioid receptor (MOR) and/or the kappa-opioid receptor (KOR), and/or the delta-opioid receptor (DOR). Products containing such compounds, as well as methods for their use and preparation, are also provided.