(R)-2-(2-噻吩基)-甘氨酸 | 65058-23-3

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 甘氨酸类衍生物
• 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: (R)-2-(2-噻吩基)-甘氨酸
• 中文别名: (R)-2-噻吩甘氨酸
• 英文名称: (R)-amino(thiophen-2-yl)acetic acid
• 英文别名: (S)-α-(2-thienyl)glycine；D-α-(2-thienyl)glycine；L-α-(2-thienyl)glycine；L-(2-Thienyl)glycin；(2R)-2-azaniumyl-2-thiophen-2-ylacetate
• CAS: 65058-23-3
• 化学式: C₆H₇NO₂S
• 分子量: 157.193
• InChiKey: XLMSKXASROPJNG-YFKPBYRVSA-N

物化性质

• 沸点：
  311.8±32.0 °C(Predicted)
• 密度：
  1.418±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  91.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• WGK Germany：
  3
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P330,P363,P501
• 危险性描述：
  H302,H312,H332

反应信息

• 作为反应物：
  描述：

  (R)-2-(2-噻吩基)-甘氨酸 在 哌啶 、 1-羟基苯并三唑 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-Quinolinecarboxamide, N-[(1R)-2-[[(1S,2R,4S)-4-[[2-(2,6-dimethylphenoxy)acetyl]amino]-2-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]amino]-2-oxo-1-(2-thienyl)ethyl]-4-hydroxy-
  参考文献：
  名称：

  Small hydroxyethylene-based peptidomimetics inhibiting both HIV-1 and C. albicans aspartic proteases

  摘要：

  We have extended a highly flexible method for rapidly assembling aspartic protease inhibitors to produce symmetric and asymmetric monohydroxyethylene peptidomimetics. This method is based on the prior synthesis of the central non-cleavable peptide-bond isostere [NH2-P(1psi)P1'-NH2; psi = hydroxyethylene isostere, HNCH(Bz)CHOHCH2CH(Bz)NH], with the possibility of accurately controlling its stereochemistry (S,S,S or S,R,S), and subsequently adding appropriate flanking units, chosen from commercially available amino acids, aromatic carboxylic acids, or phenoxyacetic acid (Poa) derivatives. The method was used to make asymmetric inhibitors of general formula Kyn-Xaa-PhepsiPhe-dmPoa, (Kyn = kynurenic acid, Xaa - Val, Thr or D-thienylglycine, M-r = 716-754) and symmetric inhibitors of formula xPoa-PhepsiPhe-xPoa (xPoa = Poa or dimethyl-, hydroxy-, formyl- or acetyl-Poa. Poa, M-r = 553-609). with logP(o/w). values ranging from 4.1 to 7.6. Inhibition of HIV-PR did not depend on the stereochemistry of the hydroxyl group, while it depended markedly on the substituents present on the Poa residues, with dmPoa being preferred over Poa or its more hydrophilic derivatives. Conversely, inhibition of Candida albicans Sap2 was higher for the S,S,S epimers, and Poa or its hydrophilic derivatives were preferred over dmPoa. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.08.004
• 作为产物：
  描述：

  (R)-2-<(2-hydroxy-1-phenylethyl)amino>-2-(2-thienyl)ethanenitrile 在 lead(IV) acetate 、 盐酸 、 氯化亚砜 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 37.3h， 生成 (R)-2-(2-噻吩基)-甘氨酸
  参考文献：
  名称：

  使用 (R)-Phenylglycinol 作为手性助剂高效实用合成 L-α-氨基酸

  摘要：

  包括 L-α-芳基甘氨酸在内的 L-α-氨基酸可以通过 (R)-2-氨基-2-苯基乙醇与醛和氰化氢的 Strecker 反应得到的 α-氨基腈方便地立体选择性地合成。这些α-氨基腈的立体选择性受热力学控制。

  DOI：

  10.1246/bcsj.65.2359

文献信息

• [EN] THIADIAZOLEDIOXIDES AND THIADIAZOLEOXIDES AS CXC- AND CC-CHEMOKINE RECEPTOR LIGANDS<br/>[FR] THIADIAZOLEDIOXYDES ET THIADIAZOLEOXIDES CONVENANT COMME LIGANDS DES RECEPTEURS DES CXC- ET CC-CHIMIOKINES
  申请人：PHARMACOPEIA INC

  公开号：WO2004033440A1

  公开（公告）日：2004-04-22

  Disclosed are novel compounds of the formula (IA) and the pharmaceutically acceptable salts and solvates thereof. Examples of groups comprising Substituent A include heteroaryl, aryl, heterocycloalkyl, cycloalkyl, aryl, alkynyl, alkenyl, aminoalkyl, alkyl or amino. Examples of groups comprising Substituent B include aryl and heteroaryl. Also disclosed is a method of treating a chemokine mediated diseases, such as, cancer, angiogenisis, angiogenic ocular diseases, pulmonary diseases, multiple sclerosis, rheumatoid arthritis, osteoarthritis, stroke and cardiac reperfusion injury, acute pain, acute and chronic inflammatory pain, and neuropathic pain using a compound of formula (IA).

  披露了公式（IA）的新颖化合物以及其中医药可接受的盐和溶剂化物。包含取代基A的基团示例包括杂芳基、芳基、杂环烷基、环烷基、芳基、炔基、烯基、氨基烷基、烷基或氨基。包含取代基B的基团示例包括芳基和杂芳基。还披露了一种治疗趋化因子介导的疾病的方法，例如，癌症、血管生成、血管生成性眼病、肺病、多发性硬化症、类风湿性关节炎、骨关节炎、中风和心脏再灌注损伤、急性疼痛、急性和慢性炎症性疼痛，以及使用公式（IA）的化合物的神经性疼痛。
• [EN] ISOTHIAZOLE DIOXIDES AS CXC- AND CC- CHEMOKINE RECEPTOR LIGANDS<br/>[FR] DIOXYDES D'ISOTHIAZOLE EN TANT QUE LIGANDS DU RECEPTEUR DE LA CHIMIOKINE CXC ET CC
  申请人：SCHERING CORP

  公开号：WO2005068460A1

  公开（公告）日：2005-07-28

  Disclosed are novel compounds of the formula (IA): and the pharmaceutically acceptable salts and solvates thereof. D and E are different groups wherein one is N and the other is CR50. Examples of groups comprising Substituent A include heteroaryl, aryl, heterocycloalkyl, cycloalkyl, aryl, alkynyl, alkenyl, aminoalkyl, alkyl or amino. Examples of groups comprising Substituent B include aryl and heteroaryl. Also disclosed is a method of treating a chemokine mediated diseases, such as, cancer, angiogenisis, angiogenic ocular diseases, pulmonary diseases, multiple sclerosis, rheumatoid arthritis, osteoarthritis, stroke and cardiac reperfusion injury, pain (e.g., acute pain, acute and chronic inflammatory pain, and neuropathic pain) using a compound of formula IA.

  公开了公式(IA)的新化合物：以及它们的药物可接受的盐和溶剂化物。D和E是不同的基团，其中一个是N，另一个是CR50。包含取代基A的基团示例包括杂芳基、芳基、杂环烷基、环烷基、芳基、炔基、烯基、氨基烷基、烷基或氨基。包含取代基B的基团示例包括芳基和杂芳基。还公开了一种治疗趋化因子介导的疾病的方法，例如，癌症、血管生成、血管生成性眼病、肺病、多发性硬化症、类风湿性关节炎、骨关节炎、中风和心肌再灌注损伤，疼痛(例如，急性疼痛、急性和慢性炎症性疼痛、神经性疼痛)使用公式IA的化合物。
• [EN] PYRAZINE AND IMIDAZOLIDINE DERIVATIVES AND THEIR USES TO TREAT HEPATITIS C<br/>[FR] DÉRIVÉS DE PYRAZINE ET D'IMIDAZOLIDINE ET LEURS UTILISATIONS EN VUE DU TRAITEMENT DE L'HÉPATITE C
  申请人：GILEAD PHARMASSET LLC

  公开号：WO2012103113A1

  公开（公告）日：2012-08-02

  Disclosed herein are compounds useful for treating a viral infection, such HCV.

  本文披露了一些用于治疗病毒感染，如HCV的化合物。
• RAPAFUCIN DERIVATIVE COMPOUNDS AND METHODS OF USE THEREOF
  申请人：The Johns Hopkins University

  公开号：US20210094933A1

  公开（公告）日：2021-04-01

  The present disclosure provides macrocyclic compounds inspired by the immunophilin ligand family of natural products FK506 and rapamycin. The generation of a Rapafucin library of macrocyles that contain FK506 and rapamycin binding domains should have great potential as new leads for developing drugs to be used for treating diseases.

  本公开提供了受免疫蛋白配体家族FK506和雷帕霉素天然产物启发的大环化合物。生成包含FK506和雷帕霉素结合结构域的Rapafucin大环化合物库，应具有作为治疗疾病新药的潜力。
• Stereoselective Synthesis of L-Amino Acids via Strecker and Ugi Reaktions on Carbohydrate Templates
  作者：Horst Kunz、Waldemar Pfrengle、Karola Rück、Wilfried Sager

  DOI：10.1055/s-1991-26641

  日期：——

  L-Amino acid derivatives are stereoselectively synthesized in high yield using 2,3,4-tri-O-pivaloyl-α-D-arabinopyranosylamine or 2,3, 4-tri- O-pivaloyl-β-L-fucopyranosylamine as the chiral auxiliary in Strecker and Ugi reactions.

  L-氨基酸衍生物在斯特克反应和乌吉反应中采用2,3,4-三-O-庚酰基-α-D-阿拉伯吡喃糖胺或2,3,4-三-O-庚酰基-β-L-岩藻糖吡喃糖胺作为手性辅助剂，立体选择性合成，产率高。