24-Methyl-23-propan-2-yloxy-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-1(13),2,4(8),9,11,14(22),15,17(21)-octaene | 1333222-85-7

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 苯并菲啶生物碱
• 英文名称: 24-Methyl-23-propan-2-yloxy-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-1(13),2,4(8),9,11,14(22),15,17(21)-octaene
• 英文别名: 24-methyl-23-propan-2-yloxy-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-1(13),2,4(8),9,11,14(22),15,17(21)-octaene
• CAS: 1333222-85-7
• 化学式: C₂₃H₂₁NO₅
• 分子量: 391.423
• InChiKey: GHZUBLRVAAABQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  49.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  血根碱 、 异丙醇 在 copper chloride dihydrate 、 氧气 作用下， 反应 10.0h， 以98%的产率得到24-Methyl-23-propan-2-yloxy-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-1(13),2,4(8),9,11,14(22),15,17(21)-octaene
  参考文献：
  名称：

  Structural Modification of Sanguinarine and Chelerythrine and Their <i>in Vitro</i> Acaricidal Activity against <i>Psoroptes cuniculi</i>

  摘要：

  血根碱（1）和白屈菜红碱（2）是两种季铵基苯并[c]菲啶生物碱（QBAs）。通过C=N+键的修饰合成了1和2的18个衍生物，并评估了它们对兔耳螨（Psoroptes cuniculi）的体外杀螨活性。开发了一种新方法制备1和2的6-烷氧基二氢衍生物（1a–e，2a–e）。在所有化合物中，只有6-烷氧基二氢血根碱（1a–e）在5.0 mg/mL浓度下显示出显著的杀螨活性，其中1a具有最强的活性（50%致死浓度（LC50）=339.70±0.75 mg/L，50%致死时间（LT50）=6.53±0.04 h），与标准药物伊维菌素（LC50=168.19±11.79 mg/L，LT50=16.54±0.11 h）相当。1和2中的亚胺基团被证实是其杀螨活性的决定因素。6-烷氧基二氢衍生物（1a–e，2a–e）是1和2的前药。与7,8-二甲氧基相比，7,8-甲基二氧基能显著提高生物活性。现有结果表明，QBAs是有前景的候选化合物或开发新型异喹啉杀螨剂的先导化合物。

  DOI：

  10.1248/cpb.c12-00618

文献信息

• In Vitro Antifungal Activity of Sanguinarine and Chelerythrine Derivatives against Phytopathogenic Fungi
  作者：Xin-Juan Yang、Fang Miao、Yao Yao、Fang-Jun Cao、Rui Yang、Yan-Ni Ma、Bao-Fu Qin、Le Zhou

  DOI：10.3390/molecules171113026

  日期：——

  In order to understand the antifungal activity of some derivatives of sanguinarine (S) and chelerythrine (C) and their structure-activity relationships, sixteen derivatives of S and C were prepared and evaluated for in vitro antifungal activity against seven phytopathogenic fungi by the mycelial growth rate method. The results showed that S, C and their 6-alkoxy dihydro derivatives S1–S4, C1–C4 and 6-cyanodihydro derivatives S5, C5 showed significant antifungal activity at 100 µg/mL against all the tested fungi. For most tested fungi, the median effective concentrations of S, S1, C and C1 were in a range of 14–50 µg/mL. The structure-activity relationship showed that the C=N+ moiety was the determinant for the antifungal activity of S and C. S1–S5 and C1–C5 could be considered as the precursors of S and C, respectively. Thus, the present results strongly suggested that S and C or their derivatives S1–S5 and C1–C5 should be considered as good lead compounds or model molecules to develop new anti-phytopathogenic fungal agents.

  为了理解血根碱（S）和白屈菜红碱（C）及其衍生物的抗真菌活性和结构-活性关系，制备并评估了十六种S和C衍生物对七种植物病原真菌的体外抗真菌活性，采用菌丝生长速率法进行测定。结果显示，S、C及其6-烷氧基二氢衍生物S1-S4、C1-C4和6-氰基二氢衍生物S5、C5在100 µg/mL浓度下对所有测试真菌均表现出显著的抗真菌活性。对于大多数测试真菌，S、S1、C和C1的中效浓度范围为14-50 µg/mL。结构-活性关系表明，C=N+部分是S和C抗真菌活性的决定因素。S1-S5和C1-C5可以分别被视为S和C的前体。因此，当前结果强烈表明，S和C或其衍生物S1-S5和C1-C5应被视为开发新型抗植物病原真菌剂的优良先导化合物或模型分子。
• Structural Modification of Sanguinarine and Chelerythrine and Their &lt;i&gt;in Vitro&lt;/i&gt; Acaricidal Activity against &lt;i&gt;Psoroptes cuniculi&lt;/i&gt;
  作者：Fang Miao、Xin-Juan Yang、Yan-Ni Ma、Feng Zheng、Xiao-Ping Song、Le Zhou

  DOI：10.1248/cpb.c12-00618

  日期：——

  Sanguinarine (1) and chelerythrine (2) are two quaternary benzo[c]phenanthridine alkaloids (QBAs). Eighteen derivatives of 1 and 2 were synthesized by modification of C=N+ bond and evaluated for their in vitro acaricidal activity against Psoroptes cuniculi, a mange mite. A new method was developed to prepare 6-alkoxy dihydro derivatives of 1 and 2 (1a–e, 2a–e). Among all the compounds, only 6-alkoxy dihydrosanguinarines (1a–e) showed significant acaricidal activity at 5.0 mg/mL and 1a possessed the strongest activity (50% lethal concentrations (LC50)=339.70±0.75 mg/L, 50% lethal time (LT50)=6.53±0.04 h), comparable with a standard drug ivermectin (LC50=168.19±11.79 mg/L, LT50=16.54±0.11 h). The iminium moiety in 1 and 2 was proven to be the determinant for their acaricidal properties. 6-Alkoxy dihydro derivatives (1a–e, 2a–e) were prodrugs of 1 and 2. Compared with 7,8-dimethoxy groups, 7,8-methylenedioxy group was able to significantly improve the bioactivity. The present results suggested that QBAs are promising candidates or lead compounds for the development of new isoquinoline acaricidal agents.

  血根碱（1）和白屈菜红碱（2）是两种季铵基苯并[c]菲啶生物碱（QBAs）。通过C=N+键的修饰合成了1和2的18个衍生物，并评估了它们对兔耳螨（Psoroptes cuniculi）的体外杀螨活性。开发了一种新方法制备1和2的6-烷氧基二氢衍生物（1a–e，2a–e）。在所有化合物中，只有6-烷氧基二氢血根碱（1a–e）在5.0 mg/mL浓度下显示出显著的杀螨活性，其中1a具有最强的活性（50%致死浓度（LC50）=339.70±0.75 mg/L，50%致死时间（LT50）=6.53±0.04 h），与标准药物伊维菌素（LC50=168.19±11.79 mg/L，LT50=16.54±0.11 h）相当。1和2中的亚胺基团被证实是其杀螨活性的决定因素。6-烷氧基二氢衍生物（1a–e，2a–e）是1和2的前药。与7,8-二甲氧基相比，7,8-甲基二氧基能显著提高生物活性。现有结果表明，QBAs是有前景的候选化合物或开发新型异喹啉杀螨剂的先导化合物。