Methyl 2-[1-[[4-bromo-6-[[2-hydroxy-1-(4-methoxycarbonyl-1,3-oxazol-2-yl)ethyl]carbamoyl]pyridine-2-carbonyl]amino]-2-hydroxyethyl]-1,3-oxazole-4-carboxylate | 1301599-32-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: Methyl 2-[1-[[4-bromo-6-[[2-hydroxy-1-(4-methoxycarbonyl-1,3-oxazol-2-yl)ethyl]carbamoyl]pyridine-2-carbonyl]amino]-2-hydroxyethyl]-1,3-oxazole-4-carboxylate
• CAS: 1301599-32-5
• 化学式: C₂₁H₂₀BrN₅O₁₀
• 分子量: 582.321
• InChiKey: YSHMCMICBNRDHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  216
• 氢给体数：
  4
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  Methyl 2-[1-[[4-bromo-6-[[2-hydroxy-1-(4-methoxycarbonyl-1,3-oxazol-2-yl)ethyl]carbamoyl]pyridine-2-carbonyl]amino]-2-hydroxyethyl]-1,3-oxazole-4-carboxylate 在 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以87%的产率得到Methyl 2-[2-[4-bromo-6-[4-(4-methoxycarbonyl-1,3-oxazol-2-yl)-4,5-dihydro-1,3-oxazol-2-yl]pyridin-2-yl]-4,5-dihydro-1,3-oxazol-4-yl]-1,3-oxazole-4-carboxylate
  参考文献：
  名称：

  结合有膦酸酯基的基于聚恶唑的大环的设计与合成

  摘要：

  我们介绍了含有膦酸酯基团的基于聚恶唑的大环化合物的设计和合成。建立了可靠的途径，该途径允许在大环周边方便且通用地引入各种膦酸酯官能团，例如膦酸酯，酸和盐。预计这种前所未有的大环化合物将成为端粒酶抑制剂的诱人候选物。

  DOI：

  10.1002/cjoc.201400213
• 作为产物：
  描述：

  2,6-bis[[[1-(4-(methoxycarbonyl)oxazol-2-yl)-2-(triisopropylsilyloxy)ethyl]amino]carbonyl]-4-bromopyridine 在 pyridine hydrofluoride 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 生成 Methyl 2-[1-[[4-bromo-6-[[2-hydroxy-1-(4-methoxycarbonyl-1,3-oxazol-2-yl)ethyl]carbamoyl]pyridine-2-carbonyl]amino]-2-hydroxyethyl]-1,3-oxazole-4-carboxylate
  参考文献：
  名称：

  Macrocyclic Pyridyl Polyoxazoles: Selective RNA and DNA G-Quadruplex Ligands as Antitumor Agents

  摘要：

  The synthesis of a series of 24-membered pyridine-containing polyoxazole macrocycles is described. Seventeen new macrocycles were evaluated for cytotoxic activity against RPMI 8402, KB-3, and KB-3 cell lines that overexpress the efflux transporters MDR1 (KBV-1) and BCRP (KBH5.0). Macrocycles in which the pyridyl-polyoxazole moiety is linked by a 1,3-bis(aminomethyl)phenyl group with a 5-(2-aminoethyl)- (18) or a 5-(2-dimethylaminoethyl)- substituent (19) displayed the greatest cytotoxic potency. These compounds exhibit exquisite selectivity for stabilizing G-quadruplex DNA with no stabilization of duplex DNA or RNA. Compound 19 stabilizes quadruplex mRNA that encodes the cell-cycle checkpoint protein kinase Aurora A to a greater extent than the quadruplex DNA of a human telomeric sequence. These data may suggest a role for G-quadruplex ligands interacting with mRNA being associated with the biological activity of macrocyclic polyoxazoles. Compound 19 has significant in vivo anticancer activity against a human breast cancer xenograft (MDA-MB-435) in athymic nude mice.

  DOI：

  10.1021/jm1000612

文献信息

• THERAPEUTIC COMPOUNDS
  申请人：LaVoie Edmond J.

  公开号：US20120238595A1

  公开（公告）日：2012-09-20

  The invention provides compounds of formula (I) wherein u, d, v, m, n, R 1 , W, X, Y, and Z have any values defined herein, as well as salts thereof. The compounds have activity as anti-proliferative agents.
• US8796300B2
  申请人：——

  公开号：US8796300B2

  公开（公告）日：2014-08-05