1-azido-13-oxo-3,6,9-trioxa-12-azahexadecan-16-oic acid | 1202400-17-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1-azido-13-oxo-3,6,9-trioxa-12-azahexadecan-16-oic acid
• 英文别名: 4-[2-[2-[2-(2-Azidoethoxy)ethoxy]ethoxy]ethylamino]-4-oxobutanoic acid
• CAS: 1202400-17-6
• 化学式: C₁₂H₂₂N₄O₆
• 分子量: 318.33
• InChiKey: IADGITLRTVYSJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  22
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-azido-13-oxo-3,6,9-trioxa-12-azahexadecan-16-oic acid 、 喜树碱 在 4-二甲氨基吡啶 、 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 36.0h， 以72%的产率得到20-(5-aza-16-azido-8,11,14-trioxa-4-oxohexadecanoyl)camptothecin
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluations of Tumor-Targeting Dual-Warhead Conjugates for a Taxoid–Camptothecin Combination Chemotherapy

  摘要：

  Novel tumor-targeting dual-warhead conjugates, 2 (DW-1) and 3 (DW-2), which consist of a next-generation taxoid, 1 (SB-T-1214), and camptothecin as two warheads, self-immolative disulfide linkers for drug release, biotin as the tumor-targeting moiety, and 1,3,5-triazine as the tripod splitter module, were designed and synthesized. The potency of 2 was evaluated against MX-1, MCF-7, ID8, L1210FR (BR+, biotin receptor overexpressed) and WI38 (BR-, normal) cell lines in the absence and presence of glutathione (GSH), which is an endogenous thiol that triggers drug release inside the cancer cells. With the GSH and resuspension protocol, 2 exhibited IC50 values of 3.22-9.80 nM against all BR+ cancer cell lines, and 705 nM against WI38. Thus, there was a two orders of magnitude higher selectivity to cancer cells. Also, a clear cooperative effect was observed for the taxoid-camptothecin combination when two drugs were delivered to the cancer cells specifically in the form of a dual-warhead conjugate.

  DOI：

  10.1021/jm500631u
• 作为产物：
  描述：

  三缩四乙二醇 在 盐酸 、 sodium azide 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 56.5h， 生成 1-azido-13-oxo-3,6,9-trioxa-12-azahexadecan-16-oic acid
  参考文献：
  名称：

  [EN] RADIOLABELLED TARGETING LIGANDS
  [FR] LIGANDS DE CIBLAGE RADIOMARQUÉS

  摘要：

  本发明涉及作为放射成像剂和放射性药物有用的化合物。这些化合物可以与放射性核素配位，并可用于诊断成像和放射治疗。该发明还涉及利用本发明的非配位和放射标记化合物的预后和治疗方法。

  公开号：

  WO2021087568A1

文献信息

• [EN] RAPAMYCIN ANALOGS AS MTOR INHIBITORS<br/>[FR] ANALOGUES DE LA RAPAMYCINE UTILISÉS EN TANT QU'INHIBITEURS DE MTOR
  申请人：REVOLUTION MEDICINES INC

  公开号：WO2018204416A1

  公开（公告）日：2018-11-08

  The present disclosure relates to rapamycin analogs of the general Formula (I). The compounds are inhibitors of mTOR and thus useful for the treatment of cancer, immune-mediated diseases and age related conditions.

  本公开涉及一般式（I）的雷帕霉素类似物。这些化合物是mTOR的抑制剂，因此对于治疗癌症、免疫介导性疾病和与年龄相关的疾病是有用的。
• Induction of apoptosis in MDA-MB-231 breast cancer cells by a PARP1-targeting PROTAC small molecule
  作者：Qiuye Zhao、Tianlong Lan、Shang Su、Yu Rao

  DOI：10.1039/c8cc07813k

  日期：——

  We report for the first time a PARP1-targeting PROTAC small molecule to selectively induce the cleavage of PARP1.

  我们首次报道了一种针对PARP1的PROTAC小分子，可以选择性地诱导PARP1的裂解。
• RAPAMYCIN ANALOGS AS MTOR INHIBITORS
  申请人：Revolution Medicines, Inc.

  公开号：EP3619216A1

  公开（公告）日：2020-03-11
• [EN] NEAR-INFRARED FLUORESCENT HEPTAMETHINE DYE CONJUGATES WITH FAVORABLE BLEACHING PROPERTIES<br/>[FR] CONJUGUÉS DE COLORANT HEPTAMÉTHINE FLUORESCENTS DANS LE PROCHE INFRAROUGE AYANT DES PROPRIÉTÉS DE BLANCHIMENT FAVORABLES
  申请人：[en]HELMHOLTZ ZENTRUM MÜNCHEN - DEUTSCHES FORSCHUNGSZENTRUM FÜR GESUNDHEIT UND UMWELT (GMBH)

  公开号：WO2023227601A1

  公开（公告）日：2023-11-30

  The present invention relates to near-infrared fluorescent heptamethine dyes of formula (I) and conjugates of such heptamethine dyes with favourable biodistribution and bleaching properties. The invention is further directed to the use of these compounds in diagnosis or in intraoperative surgery, in particular for use as contrast agents.