nicotinoylalanine | 36724-75-1

• 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: nicotinoylalanine
• 英文别名: Nicotinoyl-L-alanin；N-(pyridin-3-ylcarbonyl)-L-alanine；(2S)-2-(pyridine-3-carbonylamino)propanoic acid
• CAS: 36724-75-1
• 化学式: C₉H₁₀N₂O₃
• mdl: MFCD04112963
• 分子量: 194.19
• InChiKey: BXXVFSAYKXAKAO-LURJTMIESA-N

物化性质

• 沸点：
  492.7±25.0 °C(Predicted)
• 密度：
  1.285±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  79.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  nicotinoylalanine 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 反应 1.0h， 生成 2-(1-adamantyl)ethyl (2R)-2-[[(2S)-2-[[2-[[(2R)-2-[[(2S)-3-(4-hydroxyphenyl)-2-[[(2S)-2-(pyridine-3-carbonylamino)propanoyl]amino]propanoyl]amino]propanoyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoate
  参考文献：
  名称：

  Brain-Targeted Delivery of a Leucine-enkephalin Analogue by Retrometabolic Design

  摘要：

  A brain-targeted chemical delivery system (CDS) based on retrometabolic drug design was applied to a Leu-enkephalin analogue, Tyr-D-Ala-Gly-Phe-D-Leu (DADLE). The molecular architecture of the peptide CDS disguises its peptide nature from neuropeptide-degrading enzymes and provides lipophilic, bioreversible functions for the penetration through the blood-brain barrier. These functions were provided by a targetor, a 1,4-dihydrotrigonellyl group, on the N-terminus and a bulky, lipophilic ester group on the C-terminus. A spacer amino acid residue was also inserted between the targetor and the parent peptide to assure the release of DADLE by specific enzymes. Four CDSs were synthesized by segment-coupling method that proved to be superior to sequential elongation in obtaining this type of peptide conjugates. Intravenous injection of the compounds produced a significant and long-lasting response in rats monitored by the tail-flick latency measurements. CDSs having the bulkier cholesteryl group showed a better efficacy than those having the smaller 1-adamantaneethyl ester. The spacer was the most important factor to manipulate the rate of DADLE release and, thus, the pharmacological activity; proline as a spacer produced more potent analgesia than alanine. The antinociceptive effect of the CDSs was naloxone-reversible and methylnaloxonium-irreversible, confirming that central opiate receptors were solely responsible for mediating analgesia induced by the peptide CDS that delivered, retained, and then released the peptide in the brain.

  DOI：

  10.1021/jm960356e
• 作为产物：
  描述：

  氯化烟碱盐酸盐 在 TEA 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 nicotinoylalanine
  参考文献：
  名称：

  Brain-Targeted Delivery of a Leucine-enkephalin Analogue by Retrometabolic Design

  摘要：

  A brain-targeted chemical delivery system (CDS) based on retrometabolic drug design was applied to a Leu-enkephalin analogue, Tyr-D-Ala-Gly-Phe-D-Leu (DADLE). The molecular architecture of the peptide CDS disguises its peptide nature from neuropeptide-degrading enzymes and provides lipophilic, bioreversible functions for the penetration through the blood-brain barrier. These functions were provided by a targetor, a 1,4-dihydrotrigonellyl group, on the N-terminus and a bulky, lipophilic ester group on the C-terminus. A spacer amino acid residue was also inserted between the targetor and the parent peptide to assure the release of DADLE by specific enzymes. Four CDSs were synthesized by segment-coupling method that proved to be superior to sequential elongation in obtaining this type of peptide conjugates. Intravenous injection of the compounds produced a significant and long-lasting response in rats monitored by the tail-flick latency measurements. CDSs having the bulkier cholesteryl group showed a better efficacy than those having the smaller 1-adamantaneethyl ester. The spacer was the most important factor to manipulate the rate of DADLE release and, thus, the pharmacological activity; proline as a spacer produced more potent analgesia than alanine. The antinociceptive effect of the CDSs was naloxone-reversible and methylnaloxonium-irreversible, confirming that central opiate receptors were solely responsible for mediating analgesia induced by the peptide CDS that delivered, retained, and then released the peptide in the brain.

  DOI：

  10.1021/jm960356e

文献信息

• WATER-SOLUBLE THALIDOMIDE DERIVATIVES
  申请人：ZHANG Hesheng

  公开号：US20100240651A1

  公开（公告）日：2010-09-23

  A compound of formula (I), wherein R 1 represents H, or a C 1-4 alkyl group; R 2 represents H, a C 1-4 alkyl group, C(O)CHR 4 NR 5 R 6 , or C(O)W; or R 1 and R 2 taken together represent 1,3-propylene; R 3 represents H, a C 1-4 alkyl group, C(O)CHR 4 NR 5 R 6 , or C(O)W; or R 2 and R 3 taken together represent 1,3-propylene, 1,4-butylene, 1,5-pentylene, 1,6-hexylene, CH 2 OCH 2 , CH 2 SCH 2 or CH 2 NR 7 CH 2 , wherein R 7 represents H or a C 1-4 alkyl group; and when one of R 2 and R 3 represents H, or a C 1-4 alkyl group, the other one does not represent H; and R 8 represents H, or a C 1-4 alkyl group.

  化合物的化学式为（I），其中R1代表H或C1-4烷基；R2代表H，C1-4烷基，C（O）CHR4NR5R6或C（O）W；或R1和R2一起代表1,3-丙二基；R3代表H，C1-4烷基，C（O）CHR4NR5R6或C（O）W；或R2和R3一起代表1,3-丙二基，1,4-丁二基，1,5-戊二基，1,6-己二基，CH2OCH2，CH2SCH2或CH2NR7CH2，其中R7代表H或C1-4烷基；当R2和R3中的一个代表H或C1-4烷基时，另一个不代表H；R8代表H或C1-4烷基。
• WRINKLE-PREVENTIVE/AMELIORATING AGENT
  申请人：SHISEIDO COMPANY, LTD.

  公开号：EP1908454A1

  公开（公告）日：2008-04-09

  A wrinkle-preventing and -improving composition comprising one or more than one compound selected from the group consisting of α-amino acid derivatives represented by the following general formula (1) and salts thereof: wherein, R1 represents hydrogen atom, CH3 group or CH2OH group, R2 and R3 each independently represent hydrogen atom, alkyl group having 1 to 4 carbons, provided that R2 and R3 cannot be hydrogen atom at the same time, or R2 and R3 together with N atom to which they are bound may form a ring structure having a total carbon number of 4 to 6, in which case said ring structure may optionally contain an oxygen atom as a heteroatom, R4 represents hydrogen atom, alkyl group having 1 to 18 carbons, wherein when R1 and R4 are hydrogen atom, it cannot be that one of R2 and R3 is benzyloxycarbonyl group and the other is hydrogen atom.

  一种防皱和改善皱纹的组合物，包含一种或一种以上选自下式（1）所代表的 α-氨基酸衍生物及其盐类的化合物： 其中，R1 代表氢原子、CH3 基团或 CH2OH 基团，R2 和 R3 各自独立地代表氢原子、具有 1 至 4 个碳原子的烷基，但 R2 和 R3 不能同时为氢原子，或者 R2 和 R3 与它们所结合的 N 原子可形成一个总碳数为 4 至 6 的环结构、R4 代表氢原子或碳原子数为 1 至 18 的烷基，其中当 R1 和 R4 为氢原子时，R2 和 R3 不能一个为苄氧羰基，另一个为氢原子。
• High concentration protein formulations with reduced viscosity
  申请人：Bhami's Research Laboratory, Pvt. Ltd.

  公开号：US10646569B2

  公开（公告）日：2020-05-12

  The present disclosure, among other things, provides low-viscosity, high concentration therapeutic protein agent formulations.

  本公开的内容包括提供低粘度、高浓度的治疗性蛋白制剂。
• BRAIN-ENHANCED DELIVERY OF NEUROACTIVE PEPTIDES BY SEQUENTIAL METABOLISM
  申请人：UNIVERSITY OF FLORIDA

  公开号：EP0661986A1

  公开（公告）日：1995-07-12
• EP0661986A4
  申请人：——

  公开号：EP0661986A4

  公开（公告）日：1997-04-23