4,7-diphenyl-5-nitro-1,10-phenanthroline | 148148-97-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4,7-diphenyl-5-nitro-1,10-phenanthroline
• 英文别名: 5-nitro-4,7-diphenyl-1,10-phenanthroline
• CAS: 148148-97-4
• 化学式: C₂₄H₁₅N₃O₂
• 分子量: 377.402
• InChiKey: WRYIDKMLZPBWIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,7-diphenyl-5-nitro-1,10-phenanthroline 在 亚磷酸三乙酯 作用下， 以 十二烷 为溶剂， 反应 2.0h， 生成 18-Phenyl-2,12,15-triazapentacyclo[11.7.1.03,8.09,21.014,19]henicosa-1(20),3,5,7,9(21),10,12,14,16,18-decaene
  参考文献：
  名称：

  A two step biomimetic total synthesis of eilatin

  摘要：

  The symmetrical tetraaza heptacyclic alkaloid eilatin (1) was synthesized in a biomimetic two step reaction from catechol and monotrifluoro kynuramine (6) under oxidative conditions in the first step (aq, EtOH, NaIO3) and basic conditions (ammoniacal MeOH, DMAP) in the second. Two other unsuccessful approaches, one leading to 7-phenylascididemin, are described.

  DOI：

  10.1016/s0040-4039(00)60790-6
• 作为产物：
  描述：

  3-氯代苯丙酮 、 4-硝基邻苯二胺 以15%的产率得到4,7-diphenyl-5-nitro-1,10-phenanthroline
  参考文献：
  名称：

  A two step biomimetic total synthesis of eilatin

  摘要：

  The symmetrical tetraaza heptacyclic alkaloid eilatin (1) was synthesized in a biomimetic two step reaction from catechol and monotrifluoro kynuramine (6) under oxidative conditions in the first step (aq, EtOH, NaIO3) and basic conditions (ammoniacal MeOH, DMAP) in the second. Two other unsuccessful approaches, one leading to 7-phenylascididemin, are described.

  DOI：

  10.1016/s0040-4039(00)60790-6

文献信息

• Biological applications of alkaloids derived from the tunicate Eudistoma
  申请人：The Research Foundation of State University of New York

  公开号：US05432172A1

  公开（公告）日：1995-07-11

  Biological applications of synthetic and natural alkaloids derived from the tunicate Eudistoma sp. are disclosed. A method regulating cell growth includes contacting one or more cells with an effective concentration of a compound for regulating cell growth. These compounds include: Segoline A, Segoline B, Isosegoline A, Norosegoline, Debromoshermilamine, Eilatin, 4-methylpyrido[2,3,4-kl]acridine, pyrido[2,3,4-kl]acridine, 1-acetyl-2,6-dimethylpyrido[2,3,4-kl]acridine, and derivatives and combinations of these compounds. An effective concentration range for using these compounds can range from approximately 0.1 .mu.M to 100 .mu.M. The effective concentration range for Eilatin, the most potent of these compounds is from 0.01 .mu.M to 0.99 .mu.M, and the effective concentration range for the other compounds of the present invention is from about 1.0 .mu.M to 100 .mu.M. The method has been shown to suppress growth of tumor cells, to induce differentiation of the tumor cells, and induce reverse transformation of the tumor cells. In transformed cells, the method induces reverse transformation. The method also inhibits the proliferation of cells. The examples show that the method of the present invention affects cyclic AMP mediated biological processes. At the effective concentrations this method affects the cyclic AMP mediated biological processes of cells to achieve the results described above.

  本文披露了从海鞘Eudistoma sp.中提取的合成和天然生物碱的生物应用。一种调节细胞生长的方法包括将一种或多种化合物与细胞接触，以调节细胞生长的有效浓度。这些化合物包括：Segoline A，Segoline B，Isosegoline A，Norosegoline，Debromoshermilamine，Eilatin，4-甲基吡啶[2,3,4-kl]蒽，吡啶[2,3,4-kl]蒽，1-乙酰基-2,6-二甲基吡啶[2,3,4-kl]蒽，以及这些化合物的衍生物和组合物。使用这些化合物的有效浓度范围可从约0.1μM到100μM。这些化合物中最有效的Eilatin的有效浓度范围为0.01μM至0.99μM，而本发明中其他化合物的有效浓度范围为约1.0μM至100μM。该方法已被证明可以抑制肿瘤细胞的生长，诱导肿瘤细胞分化，并诱导肿瘤细胞的逆转化。在转化的细胞中，该方法诱导逆转化。该方法还抑制细胞增殖。实例表明，本发明的方法影响环磷酸腺苷介导的生物过程。在有效浓度下，该方法影响细胞的环磷酸腺苷介导的生物过程，以实现上述结果。
• US5432172A
  申请人：——

  公开号：US5432172A

  公开（公告）日：1995-07-11
• [EN] BIOLOGICAL APPLICATIONS OF ALKALOIDS DERIVED FROM THE TUNICATE EUDISTOMA sp.<br/>[FR] APPLICATIONS BIOLOGIQUES D'ALCALOIDES DERIVES DU TUNICIER EUDISTOMA sp.
  申请人：THE RESEARCH FOUNDATION OF STATE UNIVERSITY OF NEW YORK

  公开号：WO1994003433A1

  公开（公告）日：1994-02-17

  (EN) Biological applications of synthetic and natural alkaloids derived from the tunicate $i(Eudistoma sp.), as well as the preparation of synthetic pyridoacridines, and particularly methods for the synthesis of Eilatin are disclosed. A method regulating cell growth includes contacting one or more cells with an effective concentration of compound for regulating cell growth. These compounds include: Segoline A, Segoline B, Isosegoline A, Norosegoline, Debromoshermilamine, Eilatin, 4-methylpyrido[2,3,4-kl] acridine, pyrido[2,3,4-kl]acridine, 1-acetyl-2, 6-dimethylpyrido[2,3,4-kl]acridine, and derivatives and combinations of these compounds.(FR) L'invention se rapporte aux applications biologiques d'alcaloïdes synthétiques et naturels dérivés du tunicier $i(Eudistoma sp.), ainsi qu'à la préparation de pyridoacridines synthétiques, et plus particulièrement à des procédés de synthèse de l'Eilatine. Un procédé de régulation de la prolifération cellulaire consiste à mettre une ou plusieurs cellules en contact avec une concentration efficace d'un composé destiné à réguler la prolifération cellulaire. Ces composés sont les suivants: Ségoline A, Ségoline B, Isoségoline A, Noroségoline, Debcomoshermilamine, Eilatine, 4-méthylpyrido[2,3,4-kl]acridine, pyrido[2,3,4-kl]acridine, 1-acétyl-2, 6-diméthylpyrido[2,3,4-kl]acridine, des dérivés et des combinaisons de ces composés.
• A two step biomimetic total synthesis of eilatin
  作者：Gari Gellerman、Malca Babad、Yoel Kashman

  DOI：10.1016/s0040-4039(00)60790-6

  日期：1993.3

  The symmetrical tetraaza heptacyclic alkaloid eilatin (1) was synthesized in a biomimetic two step reaction from catechol and monotrifluoro kynuramine (6) under oxidative conditions in the first step (aq, EtOH, NaIO3) and basic conditions (ammoniacal MeOH, DMAP) in the second. Two other unsuccessful approaches, one leading to 7-phenylascididemin, are described.