p-isothiocyanatophenyl 3-O-methyl-β-L-fucopyranoside | 183882-16-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-isothiocyanatophenyl 3-O-methyl-β-L-fucopyranoside
• 英文别名: (2R,3S,4R,5R,6S)-2-(4-isothiocyanatophenoxy)-4-methoxy-6-methyloxane-3,5-diol
• CAS: 183882-16-8
• 化学式: C₁₄H₁₇NO₅S
• 分子量: 311.359
• InChiKey: RUKOXNXIMFAGDD-NIXGCWMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  p-isothiocyanatophenyl 3-O-methyl-β-L-fucopyranoside 在 哌啶 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 ((S)-6-Amino-2-{3-[4-((2R,3S,4R,5R,6S)-3,5-dihydroxy-4-methoxy-6-methyl-tetrahydro-pyran-2-yloxy)-phenyl]-thioureido}-hexanoylamino)-acetic acid (S)-4-ethyl-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-4-yl ester
  参考文献：
  名称：

  Design and Optimization of 20-O-Linked Camptothecin Glycoconjugates as Anticancer Agents

  摘要：

  To improve the biological profile of 20(S)-camptothecin, a novel class of 20-O-linked camptothecin glycoconjugates has been designed for preferential cellular uptake into tumor cells by an active transport mechanism. Such conjugates have been optimized for enhanced solubility, stabilization of the camptothecin lactone ring, sufficient hydrolytic and proteolytic stability, and for an overall improvement in tumor selectivity. The constitution of the peptide spacer has a major impact on stability and biological activity of the conjugates both in vitro and in vivo, Glycoconjugates 17-22 with valine residues at the linkage position to camptothecin are sufficiently stable and show good antitumor activity in vitro against HT29 and other tumor cell lines. Fluorescence microscopy and flow cytometry experiments indicate that glycoconjugates such as 19 are taken up into lysosomal compartments of the tumor cell line HT29 by an active transport mechanism. The steric configuration of the particular amino acid residues linked to the camptothecin moiety has a major impact on the in vivo activity of the corresponding glycoconjugates in the breast cancer xenograft MX-1 model. Inhibiting tumor growth by > 96%, the glycoconjugates 19 and 21 show the best activity in this particular model and have been investigated more extensively. The glycoconjugate 19 compares favorably to topotecan 4 and glycoconjugate 21 with respect to toxicity against hematopoietic stem cells and hepatocytes. Based on its profile, 19 has been selected for clinical trials.

  DOI：

  10.1021/jm010893l
• 作为产物：
  描述：

  p-aminophenyl 3-O-methyl-β-L-fucopyranoside 生成 p-isothiocyanatophenyl 3-O-methyl-β-L-fucopyranoside
  参考文献：
  名称：

  20(S) camptothecin glycoconjugates

  摘要：

  本发明涉及20(S)-喜树碱的糖蛋白，其中3-O-甲基化的β-L-岩藻糖单元通过硫脲修饰的肽间隔连接到喜树碱衍生物的20-羟基基团。此外，本发明还涉及制备本发明化合物的方法以及它们作为药物的用途，特别是与肿瘤相关的用途。

  公开号：

  US06506734B1
• 作为试剂：
  描述：

  p-isothiocyanatophenyl 3-O-methyl-β-L-fucopyranoside 、 20-O-[L-Histidyl-L-valyl]-camptothecin trifluoroacetate 在 p-isothiocyanatophenyl 3-O-methyl-β-L-fucopyranoside 作用下， 生成 Afeletecan hydrochloride
  参考文献：
  名称：

  20(S) camptothecin glycoconjugates

  摘要：

  本发明涉及20(S)-喜树碱的糖蛋白，其中3-O-甲基化的β-L-岩藻糖单元通过硫脲修饰的肽间隔连接到喜树碱衍生物的20-羟基基团。此外，本发明还涉及制备本发明化合物的方法以及它们作为药物的用途，特别是与肿瘤相关的用途。

  公开号：

  US06506734B1

文献信息

• [DE] SUBSTITUIERTE DIHYDROCHINAZOLINE MIT ANTIVIRALEN EIGENSCHAFTEN<br/>[EN] SUBSTITUTED DIHYDROCHINAZOLINES HAVING ANTIVIRAL PROPERTIES<br/>[FR] DIHYDROQUINAZOLINES SUBSTITUEES A PROPRIETES ANTIVIRALES
  申请人：BAYER HEALTHCARE AG

  公开号：WO2004096778A1

  公开（公告）日：2004-11-11

  Die Erfindung betrifft substituierte Dihydrochinazoline der Formel (I) und Verfahren zu ihrer Herstellung sowie ihre Verwendung zur Herstellung von Arzneimitteln zur Behandlung und/oder Prophylaxe von Krankheiten, insbesondere zur Verwendung als antivirale Mittel, insbesondere gegen Cytomegaloviren.

  该发明涉及式(I)的取代二氢喹唑啉以及其制备方法和用于制备治疗和/或预防疾病的药物的用途，特别是用作抗病毒剂，特别是针对巨细胞病毒的用途。
• Substituted dihydroquinazolines
  申请人：Bayer HealthCare AG

  公开号：US07196086B2

  公开（公告）日：2007-03-27

  The invention relates to substituted dihydroquinazolines and to processes for their preparation and also to their use for preparing medicaments for the treatment and/or prophylaxis of diseases, in particular for use as antiviral agents, in particular against cytomegalo viruses.

  该发明涉及取代二氢喹唑啉及其制备方法，以及其用于制备药物治疗和/或预防疾病，特别是用作抗病毒剂，特别是针对巨细胞病毒的用途。
• Lerchen, Hans-Georg; Von Dem Bruch, Karsten, Journal fur Praktische Chemie (Weinheim), 2000, vol. 342, # 8, p. 753 - 760
  作者：Lerchen, Hans-Georg、Von Dem Bruch, Karsten

  DOI：——

  日期：——
• GLYCOKONJUGATE VON 20(S)-CAMPTOTHECIN
  申请人：Bayer HealthCare AG

  公开号：EP0981542B1

  公开（公告）日：2004-08-04
• US6506734B1
  申请人：——

  公开号：US6506734B1

  公开（公告）日：2003-01-14