2,9-dimethyl-1,10-phenanthroline hydrate | 34302-70-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: 2,9-dimethyl-1,10-phenanthroline hydrate
• 英文别名: 2,9-dimethyl-1,10-phenantroline monohydrate；neocuproine hydrate；2,9-dimethylphenanthroline monohydrate；2,9-dimethyl-1,10-phenanthroline；2,9-dimethyl-1,10-phenanthroline monohydrate；neocuproin monohydrate；dmphen monohydrate；neocuproine；2,9-dimethyl-1,10-phenanthroline;hydrate
• CAS: 34302-70-0
• 化学式: C₁₄H₁₂N₂*H₂O
• 分子量: 226.278
• InChiKey: MFZBSWSCIWCRKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  26.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,9-dimethyl-1,10-phenanthroline hydrate 以 氯仿 、 氘代甲醇 、 甲苯 为溶剂， 生成 (2,9-dimethylphenanthroline) zinc ethanethiolate methyl sulfate
  参考文献：
  名称：

  （新铜蛋白）锌硫醇盐：尝试模拟钴胺素独立的蛋氨酸合酶

  摘要：

  几种新的配合物 [(neo)Zn(SR)2] [neo = neocuproin (2,9-二甲基菲咯啉)] 已被合成和结构表征。它们以逐步的方式与烷化剂 CH3I 和 (CH3)2SO4 反应，得到硫醚 CH3SR，首先得到混合配合物 [(neo)Zn(SR)X] (X = I, CH3SO4)，然后得到 [(neo)ZnX2 ]。在非极性介质中，苄基碘会发生类似的烷基化反应，但磷酸三甲酯不会发生类似的烷基化反应。在这些条件下，硫醇盐与 [PPN] SR 的交换不会发生，这表明烷基化发生在锌结合的硫醇盐上。在极性溶剂（甲醇、DMSO）中，硫醇盐交换很容易发生，并且在较高温度下 (CH3)3PO4 也充当烷基化剂，这表明在这些条件下，溶液中存在游离的硫醇盐。定性动力学数据支持非极性介质中的缔合烷基化机制和极性介质中机制的变化。(© Wiley-VCH Verlag GmbH & Co. KGaA

  DOI：

  10.1002/ejic.200300501
• 作为试剂：
  描述：

  2,4-二甲基-1-碘苯 、 8-巯基腺嘌呤 在 copper(l) iodide 、 2,9-dimethyl-1,10-phenanthroline hydrate 、 sodium t-butanolate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 8-(2,4-dimethyl-phenylsulfanyl)adenine
  参考文献：
  名称：

  Structure–Activity Relationship in a Purine-Scaffold Compound Series with Selectivity for the Endoplasmic Reticulum Hsp90 Paralog Grp94

  摘要：

  Grp94 is involved in the regulation of a restricted number of proteins and represents a potential target in a host of diseases, including cancer, septic shock, autoimmune diseases, chronic inflammatory conditions, diabetes, coronary thrombosis, and stroke. We have recently identified a novel allosteric pocket located in the Grp94 N-terminal binding site that can be used to design ligands with a 2-log selectivity over the other Hsp90 paralogs. Here we perform extensive SAR investigations in this ligand series and rationalize the affinity and paralog selectivity of choice derivatives by molecular modeling. We then use this to design 18c, a derivative with good potency for Grp94 (IC50 = 0.22 mu M) and selectivity over other paralogs (>100- and 33-fold for Hsp90 alpha/beta and Trap-1, respectively). The paralog selectivity and target-mediated activity of 18c was confirmed in cells through several functional readouts. Compound 18c was also inert when tested against a large panel of kinases. We show that 18c has biological activity in several cellular models of inflammation and cancer and also present here for the first time the in vivo profile of a Grp94 inhibitor.

  DOI：

  10.1021/acs.jmedchem.5b00197

文献信息

• HSP90 Inhibitors Containing a Zinc Binding Moiety
  申请人：Qian Changgeng

  公开号：US20080234297A1

  公开（公告）日：2008-09-25

  The present invention relates to HSP90 inhibitors and their use in the treatment of cell proliferative diseases such as cancer. The said derivatives may further act as HDAC inhibitors.

  本发明涉及HSP90抑制剂及其在治疗癌症等细胞增殖性疾病中的应用。所述衍生物还可能作为HDAC抑制剂。
• FUSED AMINO PYRIDINE AS HSP90 INHIBITORS
  申请人：Cai Xiong

  公开号：US20080234314A1

  公开（公告）日：2008-09-25

  The present invention relates to HSP90 inhibitors containing fused amino pyridine core that are useful as inhibitors of HSP90 and their use in the treatment of HSP90 related diseases and disorders such as cancer, an autoimmune disease, or a neurodegenerative disease.

  本发明涉及含有融合氨基吡啶核的HSP90抑制剂，可用作HSP90的抑制剂，以及它们在治疗HSP90相关疾病和紊乱，如癌症、自身免疫疾病或神经退行性疾病中的用途。
• FUSED AMINO PYRIDINES FOR THE TREATMENT OF BRAIN TUMORS
  申请人：Cai Xiong

  公开号：US20100184801A1

  公开（公告）日：2010-07-22

  The present invention relates to the use of compounds with fused amino pyridine core for the treatment of malignancies associated with brain and lung. The oral administration of compounds of the instant application results in effective brain penetration and provides for non-intrusive treatment of brain and lung tumors.

  本发明涉及使用具有融合氨基吡啶核的化合物治疗与大脑和肺部相关的恶性肿瘤。本申请的化合物经口给药可有效穿透大脑，并提供对大脑和肺部肿瘤的非侵入性治疗。
• Fused Amino Pyridines for the Treatment of Lung Cancer
  申请人：Curis, Inc.

  公开号：US20160317508A1

  公开（公告）日：2016-11-03

  The present invention relates to the use of compounds with fused amino pyridine core for the treatment of malignancies associated with brain and lung. The oral administration of compounds of the instant application results in effective brain penetration and provides for non-intrusive treatment of brain and lung tumors.

  本发明涉及使用具有融合氨基吡啶核的化合物治疗与大脑和肺部相关的恶性肿瘤。本申请的化合物经口服后能有效穿透大脑，并实现对大脑和肺部肿瘤的非侵入性治疗。
• C,O-Chelates of the Trifluoroacetylacetonate Dianion with Palladium(II). Molecular Structure of [Pd(tfac(2–)-<i>C</i>,<i>O</i>)(PPh₃)(2,6-Me₂-py)]
  作者：Seichi Okeya、Yasuo Kawakita、Shinichi Matsumoto、Yukio Nakamura、Shinichi Kawaguchi、Nobuko Kanehisa、Kunio Miki、Nobutami Kasai

  DOI：10.1246/bcsj.55.2134

  日期：1982.7

  Reactions of bis(trifluoroacetylacetonato)palladium(II), [Pd(tfac)2], with tertiary phosphines followed by pyridine or its derivatives afforded a series of the [Pd(tfac(2–)-C,O)LL′]-type complexes which contain a C,O-chelating trifluoroacetylacetonate dianion and a couple of tertiary phosphine and/or heterocyclic nitrogen base ligands (L and L′). Their structures in solution were studied by 1H, 13C, 19F

  双（三氟乙酰丙酮）钯（II），[Pd(tfac)2]，与叔膦和吡啶或其衍生物的反应提供了一系列 [Pd(tfac(2-)-C,O)LL']-型配合物，包含 C,O 螯合三氟乙酰丙酮酸二价阴离子和一对叔膦和/或杂环氮碱基配体（L 和 L'）。它们在溶液中的结构通过 1H、13C、19F 和 31P NMR 光谱以及 [Pd(tfac(2-)-C,O)(PPh3)(2,6-Me2-py) ]·含有三苯基膦和2,6-二甲基吡啶作为L和L'的C6H6通过X射线衍射测定。