1-hydroxy-6-(2-ethoxy-2-oxoethoxy)phenazine 5,10-dioxide | 33859-16-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-hydroxy-6-(2-ethoxy-2-oxoethoxy)phenazine 5,10-dioxide
• 英文别名: (6-hydroxy-5,10-dioxy-phenazin-1-yloxy)-acetic acid ethyl ester；Ethyl 2-(6-hydroxy-5,10-dioxidophenazine-5,10-diium-1-yl)oxyacetate
• CAS: 33859-16-4
• 化学式: C₁₆H₁₄N₂O₆
• 分子量: 330.297
• InChiKey: VQSJAXCAIRCQQI-UHFFFAOYSA-N

物化性质

• 沸点：
  592.2±60.0 °C(predicted)
• 密度：
  1.45±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1,6-二羟基吩嗪 在 18-冠醚-6 、 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 8.5h， 生成 1-hydroxy-6-(2-ethoxy-2-oxoethoxy)phenazine 5,10-dioxide
  参考文献：
  名称：

  吩嗪5,10-二氧化物天然产物碘丁宁，粘菌素及其衍生物的全合成和抗白血病评价。

  摘要：

  吩嗪5,10-二氧化物天然产物碘和粘菌素以及由它们衍生的新化合物的新有效全合成方法只需几个步骤即可完成，其中关键步骤是1,6-二羟基吩嗪二-N-氧化。由碘丁宁制备的类似物，包括粘菌素和2-乙氧基-2-氧代乙氧基衍生物，在大气和低氧水平下完全保留了对人类癌细胞（MOLM-13白血病）的细胞毒作用。此外，碘首次首次显示出对缺氧的选择性。白血病细胞死亡诱导的构效关系表明，N-氧化物功能水平对细胞毒性至关重要。还揭示了活性仅需要两种酚官能团中的一种，从而使另一种酚官能团被修饰而没有效力的损失。

  DOI：

  10.1016/j.bmc.2017.02.058

文献信息

• Substituted phenazines and methods of treating cancer and bacterial diseases
  申请人：Rongved Pål

  公开号：US11046678B2

  公开（公告）日：2021-06-29

  Compounds of formula (Ia) or (Ib), or a pharmaceutically acceptable salt thereof, pharmaceutical compositions comprising the compounds, and methods of treatment using the compounds.

  式 (Ia) 或 (Ib) 的化合物，或其药学上可接受的盐、 包含这些化合物的药物组合物，以及使用这些化合物的治疗方法。
• N-OXIDE HETEROCYCLES FOR USE IN THE TREATMENT OF CANCER AND BACTERIAL DISEASES
  申请人：Rongved, Pål

  公开号：EP3555052A1

  公开（公告）日：2019-10-23
• COMPOUNDS
  申请人：RONGVED Pål

  公开号：US20200095237A1

  公开（公告）日：2020-03-26

  The invention provides compounds of general formula (I′), and their pharmaceutically acceptable salts: wherein: Z is a group having the formula: -T-S-A-Y in which: T is a group selected from —O—, —NH—, —S—, —(XCR 7 R 8 )— (where R 7 and R 8 is independently —H or C 1-3 alkyl and X is selected from from —O—, —NH—, —S—); S is —(C═O)—, —(SO 2 )—, —(PO 2 )—; A, —O—, —NH—, —S— or —NH(CO)—, —(CR 7 R 8 X)— (where R 7 and R 8 is independently —H or C 1-3 alkyl and X is selected from from —O—, —NH—, —S—), -T-S-A- is a group susceptible to hydrolytic and/or enzymatic cleavage in vivo to leave a group selected from —OH, —NH 2 , —SH, —COOH, —CONH 2 , —O—(CR 7 R 8 )—COOH and —(CR 7 R 8 )—CONH 2 ; Y is one or more targeting groups or a lipophilic or hydrophilic group affecting the solubility in water and the biodistribution in a living organism or a living cell; R 1 -R 6 are independently selected from hydrogen, halogen (e.g. F, Cl, Br, I), lower alkyl (e.g. C 1-6 alkyl), optionally substituted with an acidic group which is —COOH, —SO 3 H, —PO 3 H 2 or —B(OH) 2 . Such compounds find particular use as anti-neoplastic and anti-infective agents.
• SUBSTITUTED PHENAZINES AND METHODS OF TREATING CANCER AND BACTERIAL DISEASES
  申请人：Rongved Pål

  公开号：US20210292313A1

  公开（公告）日：2021-09-23

  A combination product comprising a carbapenem and a compound of formula (I′), or a pharmaceutically acceptable salt thereof: a pharmaceutical composition comprising the combination product; and methods of treating bacterial or fungal infections using the combination product and pharmaceutical composition.
• [EN] N-OXIDE HETEROCYCLES FOR USE IN THE TREATMENT OF CANCER AND BACTERIAL DISEASES<br/>[FR] HÉTÉROCYCLES N-OXYDE POUR UTILISATION DANS LE TRAITEMENT DU CANCER ET DES MALADIES BACTÉRIENNES
  申请人：UNIV OSLO

  公开号：WO2018109504A1

  公开（公告）日：2018-06-21

  The invention provides compounds of general formula (P), and their pharmaceutically acceptable salts: (Formula (I')) wherein X is an N-oxide functionality (N+-0"), or CH; Z is a group susceptible to hydrolytic and/or enzymatic cleavage in vivo to form a group selected from -OH, -COOH, -CONH2, -O-Q-COOH and -0-Q-CONH2 (where Q is a straight chained or branched alkylene group, preferably Ci-3 alkylene, e.g. methylene), and Z is optionally linked to one or more targeting groups; Ri and R2 are independently selected from hydrogen, lower alkyl (e.g. C1 -6 alkyl), halogen (e.g. F, CI, Br, I), an acidic group which is -COOH, -S03H, -P03H2 or -B(OH)2; and an aryl group (e.g. phenyl); or R] and R2, together with the intervening carbon atoms, form an optionally substituted aromatic group; each W is independently selected from lower alkyl (e.g. Ci-6 alkyl), halogen (e.g. F, CI, Br, I), OH, and an acidic group which is -COOH, -S03H, -P03H2 or -B(OH)2; and p is an integer from 0 to 3. Such compounds find particular use as anti-neoplastic and anti-infective agents.