β-carboline potassium salt | 138428-44-1

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: β-carboline potassium salt
• CAS: 138428-44-1
• 化学式: C₁₃H₉N₂O₂*K
• 分子量: 264.325
• InChiKey: ZONGVSFZYXVGMH-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.99
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  68.81
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  β-carboline potassium salt 在 lithium aluminium tetrahydride 、 二苯基磷酸 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 1-(2-Azepan-1-yl-ethyl)-9H-β-carboline
  参考文献：
  名称：

  Manzamine C congeners with modified azacyclic rings: Synthesis and biological evaluation

  摘要：

  Manzamine C congeners with modified azacyclic rings were synthesized using a DPPA-promoted conjunction of the beta-carboline-1-acetate salt with various amines as a key reaction. A preliminary biological evaluation revealed that these analogues retained similar activities as Manzamine C. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00460-x
• 作为产物：
  描述：

  色胺 在 palladium on activated charcoal 氢氧化钾 、 sodium hydroxide 、 三氯氧磷 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 15.17h， 生成 β-carboline potassium salt
  参考文献：
  名称：

  Manzamine C及其几何异构体的全合成

  摘要：

  Manzamine C（1）是由甲硅烷基氧乙烯（3）沿以下路线合成的：4→5→8→18→1。总产率为21％。通过14的Bischler-Napieralski反应，然后进行脱水，可得到Thrβ-咔啉链段（11）。通过类似的步骤，已经合成了反式异构体2和二氢马扎明C（21）。

  DOI：

  10.1016/s0040-4020(01)91003-8

文献信息

• Design, synthesis and DNA cleaving profiles of hybrids containing the novel enediyne and naturally occurring DNA intercalates
  作者：Kazunobu Toshima、Kazumi Ohta、Aya Ohashi、Takatsugu Nakamura、Masaya Nakata、Shuichi Matsumura

  DOI：10.1039/c39930001525

  日期：——

  The designed hybrids 5–11 containing the DNA cleavable enediyne 4 and naturally occurring DNA intercalators 12–18cleave DNA effectively under alkaline conditions without any additive; the hybrids 5 and 11 exhibit the strongest DNA-cleaving abilities with the identical high purine base (G>A) selectivities for their DNA-cleavage profiles.

  所设计的杂种5 - 11含有该DNA可切割的烯二炔4和天然存在的DNA嵌入剂12 - 18有效下没有任何添加剂的碱性条件下切割DNA; 杂种5和11表现出最强的DNA切割能力，并具有相同的高嘌呤碱基（G> A）选择性，可用于其DNA切割过程。
• Molecular Design, Chemical Synthesis, and Study of Novel Enediyne-Sulfide Systems Related to the Neocarzinostatin Chromophore
  作者：Kazunobu Toshima、Kazumi Ohta、Aya Ohashi、Takatsugu Nakamura、Masaya Nakata、Kuniaki Tatsuta、Shuichi Matsumura

  DOI：10.1021/ja00122a012

  日期：1995.5

  The design and synthesis of the novel monocyclic enediyne-sulfide systems and their chemical and DNA cleavage properties are described. The parent enediyne-sulfide 6 possessing a hydroxy group at the allylic position was effectively synthesized via the cross-coupling of the cis-vinyl iodide 11 and the acetylene derivative 12 using a Pd(O)-Cu(I) catalyst and the cyclization reaction of the acyclic dibromide 20 employing sodium sulfide as the key steps. In addition, the esterifications of 6 using appropriate procedures provided a series of its simple derivatives 21-29 and the hybrids 38-44 containing naturally occurring intercalators, all of which are quite stable when handled at ambient temperature. The representative enediyne-sulfide 22 was smoothly aromatized by 1,8-diazabicyclo[5.4.0]undec-7-ene in cyclohexa-1,4-diene through radical pathways and by a hydroxy anion in dimethyl sulfoxide-Tris-HCl, pH 8.5 buffer through a polar pathway. Furthermore, it was clearly found that all enediyne-sulfides cleaved DNA under alkaline conditions without any additive and the hybrids 38 and 44, each of which has the aromatic moiety of the neocarzinostatin chromophore and manzamins, respectively, exhibited the strongest DNA cleaving abilities with the identical high purine base (G > A) selectivity.
• The use of the Ramberg–Bäcklund rearrangement for the formation of aza-macrocycles: a total synthesis of manzamine C
  作者：David I. MaGee、Ellen J. Beck

  DOI：10.1139/cjc-78-8-1060

  日期：——

  A total synthesis of the marine alkaloid manzamine C has been accomplished. A Ramberg-Backlund reaction was used as a key step to construct the required azacycloundecene ring.