6-丙酮基二氢血根碱 | 37687-34-6

• 物质功能分类: 天然产物 - 生物碱
• 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
• 中文名称: 6-丙酮基二氢血根碱
• 英文名称: (+/-)-6-acetonyldihydrosanguinarine
• 英文别名: 6-acetonyl-5,6-dihydrosanguinarine；6-Acetonyldihydrosanguinarine；8-acetonyldihydrosanguinarine；6-acetonylsanguinarine；1-(13-methyl-13,14-dihydro-[1,3]dioxolo[4,5-i][1,3]dioxolo[4'5':4,5]benzo[1,2-c]phenanthridin-14-yl)-propan-2-one；1,3-Bis(11-hydrosanguinarinyl)aceton；1-(24-methyl-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)-octaen-23-yl)propan-2-one
• CAS: 37687-34-6
• 化学式: C₂₃H₁₉NO₅
• 分子量: 389.408
• InChiKey: ONEHMWWDDDSJBB-UHFFFAOYSA-N

物化性质

• 沸点：
  597.3±50.0 °C(Predicted)
• 密度：
  1.367±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。
• 物理描述：
  Solid
• 熔点：
  194-195.5°C

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  6

制备方法与用途

6-乙酰二氢血根碱是从白屈菜地上部分分离获得的一种化合物。[1]

反应信息

• 作为产物：
  描述：

  血根碱 、 丙酮 在 sodium carbonate 作用下， 生成 6-丙酮基二氢血根碱
  参考文献：
  名称：

  罂粟愈伤组织生物碱

  摘要：

  摘要 Norsanguinarine (I)，一种新的生物碱和 6-acetonyldihydrosanguinarine (II)，似乎是一种人工制品，已从罂粟的愈伤组织组织中分离出来。还检测到血根碱 (III)、二氢血根碱 (IV)、氧血根碱 (V)、丙氨酸 (VI)、隐碱 (VII)、木兰素 (VIII) 和胆碱 (IX)。

  DOI：

  10.1016/0031-9422(72)80101-8

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 antibacterial activity
  作者：Fang Miao、Xin-Juan Yang、Le Zhou、Hai-Jun Hu、Feng Zheng、Xu-Dong Ding、Dong-Mei Sun、Chun-Dong Zhou、Wei Sun

  DOI：10.1080/14786419.2010.482055

  日期：2011.5

  In this study, five derivatives of sanguinarine (1) and chelerythrine (2) were prepared, with 1 and 2 as starting materials, by reduction, oxidation and nucleophilic addition to the iminium bond C=N+. The structures of all compounds were elucidated on account of their MS, 1H-NMR and 13C-NMR data. The antibacterial activities of all compounds were screened, using Staphylococcus aureus, Escherichia coli, Aeromonas hydrophila and Pasteurella multocida as test bacteria. The minimum bacteriostatic concentration and minimum bactericidal concentration of the active compounds were determined by the turbidity method. The structure-activity relationships of 1 and 2 were discussed. The results showed that 1, 2 and their pseudoalcoholates were found to be potent inhibitors to S. aureus, E. coli and A. hydrophila, while the other derivatives were found to be inactive. The pseudoalcoholates might be the prodrugs of 1 and 2. The iminium bond in the molecules of 1 or 2 was the determinant for antibacterial activity, and the substituents at the 7 and 8 positions influenced the antibacterial activities of 1 and 2 against different bacteria.
• Alkaloids from callus tissue of Papaver somniferum
  作者：T. Furuya、A. Ikuta、K. Syōno

  DOI：10.1016/0031-9422(72)80101-8

  日期：1972.10

  Abstract Norsanguinarine (I), a new alkaloid and 6-acetonyldihydrosanguinarine (II), which appears to be an artefact, have been isolated from callus tissue of opium poppy. Sanguinarine (III), dihydrosanguinarine (IV), oxysanguinarine (V), protopine (VI), cryptopine (VII), magnoflorine (VIII) and choline (IX) have also been detected.

  摘要 Norsanguinarine (I)，一种新的生物碱和 6-acetonyldihydrosanguinarine (II)，似乎是一种人工制品，已从罂粟的愈伤组织组织中分离出来。还检测到血根碱 (III)、二氢血根碱 (IV)、氧血根碱 (V)、丙氨酸 (VI)、隐碱 (VII)、木兰素 (VIII) 和胆碱 (IX)。