tetraethyl [(6-bromopyridin-2-ylamino)methylene]bis(phosphonate) | 1365537-96-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: tetraethyl [(6-bromopyridin-2-ylamino)methylene]bis(phosphonate)
• 英文别名: N-[bis(diethoxyphosphoryl)methyl]-6-bromopyridin-2-amine
• CAS: 1365537-96-7
• 化学式: C₁₄H₂₅BrN₂O₆P₂
• 分子量: 459.214
• InChiKey: IXKVYTHQWORSQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  96
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-氨基-6-溴吡啶 、 原甲酸三乙酯 、 亚磷酸二乙酯 以 甲苯 为溶剂， 反应 72.0h， 生成 tetraethyl [(6-bromopyridin-2-ylamino)methylene]bis(phosphonate)
  参考文献：
  名称：

  Design and Synthesis of Active Site Inhibitors of the Human Farnesyl Pyrophosphate Synthase: Apoptosis and Inhibition of ERK Phosphorylation in Multiple Myeloma Cells

  摘要：

  Human farnesyl pyrophosphate synthase (hFPPS) controls intracellular levels of FPP and post-translational prenylation of small GTPase proteins, which are essential for cell signaling and cell proliferation. Clinical investigations provide evidence that N-BP inhibitors of hFPPS are disease modifying agents that improve survival of multiple myeloma (MM) patients via mechanisms unrelated to their skeletal effects. A new series of N-BPs was designed that interact with a larger portion of the GPP subpocket, as compared to the current therapeutic drugs, and rigidify the (KRRK367)-K-364 tail of hFPPS in the closed conformation in the absence of IPP. An analogue of this series was used to demonstrate inhibition of the intended biological target, resulting in apoptosis and down-regulation of ERK phosphorylation in human MM cell lines.

  DOI：

  10.1021/jm201657x

文献信息

• Nano ZnO catalyzed green synthesis and cytotoxic assay of pyridinyl and pyrimidinyl bisphosphonates
  作者：Gundluru Mohan、Sarva Santhisudha、Nadiveedhi Maheshwara Reddy、Tellamekala Sreekanth、Sudileti Murali、Cirandur Suresh Reddy

  DOI：10.1007/s00706-017-2000-2

  日期：2017.10

  A straight forward approach ensuring the anchoring of bisphosphonate moiety onto various pyridinyl and pyrimidinyl amines is described by the three-component reaction of an amine, diethyl phosphite, and triethyl orthoformate in the presence of catalytic amount of nano ZnO as an environmentally benign and heterogeneous catalyst under solvent-free microwave irradiation conditions. All the synthesized compounds are evaluated for anti-cell proliferation activity against human breast (MCF-7), prostate (DU-145), osteosarcoma (MG-63), fibrosarcoma (HT-1080), multiple myeloma (RPMI-8226) cancer cell lines using sulforhodamine-B (SRB) assay method, and adriamycin as a reference drug. All the title compounds showed promising cytotoxic activity on the five cell lines. One compound was two times more active than adriamycin on all the five cancer cell lines.[GRAPHICS].