chelilutine chloride | 30044-83-8

• 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: chelilutine chloride
• 英文别名: chelilutine；1,2,4-trimethoxy-12-methyl-[1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridinium; chloride；1,2,4-Trimethoxy-12-methyl-[1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridinium; Chlorid；chelilutinium; chloride；1,2,4-Trimethoxy-12-methyl-[1,3]benzodioxolo[5,6-c]phenanthridin-12-ium;chloride
• CAS: 30044-83-8
• 化学式: C₂₂H₂₀NO₅*Cl
• 分子量: 413.858
• InChiKey: ZXJPFZLKMLDMCZ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.73
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  50
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  chelilutine chloride 在 甲醇 、 sodium tetrahydroborate 作用下， 以89 %的产率得到dihydrochelilutine
  参考文献：
  名称：

  苯并 [c] 菲啶生物碱的集体全合成通过顺序过渡金属催化的盆栽经济方法

  摘要：

  在构建 C 和 B 环的基础上，通过连续过渡金属催化反应和灵活条件控制的曼尼希反应，通过三锅以 25-34% 的产率集体全合成了 10 个苯并 [ c ] 菲啶，这提供了一个通过盆栽经济方法生产苯并[ c ]菲啶的有效途径。

  DOI：

  10.1021/acs.orglett.2c03278
• 作为产物：
  描述：

  N-(6-bromonaphtho[2,3-d][1,3]dioxol-5-yl)-2-hydroxy-2-methylpropionamide 在 palladium diacetate 、 sodium hydroxide 、 sodium hydride 、 sodium carbonate 、 三苯基膦 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 反应 7.75h， 生成 chelilutine chloride
  参考文献：
  名称：

  通用合成全芳族苯并[ c ]菲啶生物碱

  摘要：

  描述了一种合成苯并[ c ]菲啶生物碱的通用新方法，并通过制备八种不同的生物碱加以说明。关键步骤是Smiles重排，可以轻松地从2-溴-1-萘酚中获得2-溴-1-萘胺，以及通过Suzuki偶联器连接D环单元。

  DOI：

  10.1016/s0040-4020(98)00540-7

文献信息

• Chemical Transformation of Protoberberines. XVII. Biomimetic Introduction of an Oxy Functionality at the C-10 Position in the Benzo(c)phenanthridine Skeleton: Synthesis of 2,3,7,8,10-Pentaoxygenated Benzo(c)phenanthridine Alkaloids, Chelilutine and Sanguilutine.
  作者：Miyoji HANAOKA、Won Jea CHO、Shuji YOSHIDA、Chisato MUKAI

  DOI：10.1248/cpb.39.1163

  日期：——

  An efficient and biomimetic introduction of an oxy functionality at the C-10 position in the benzo[c]phenanthridine skeleton was developed by regioselective oxygenation with salcomine-oxygen. This biomimetic procedure was successfully applied to a synthesis of 2, 3, 7, 8, 10-pentaoxygenated benzo[c]phenanthridine alkaloids, chelilutine (8) and sanguilutine (18), from the corresponding 2, 3, 7, 8-tetraoxygenated benzo[c]phenanthridines.

  开发了一种高效且仿生的方法，通过区域选择性氧化使用salcomine-氧气，在苯并[c]菲那喹类骨架的C-10位引入氧功能团。该仿生程序成功应用于合成2, 3, 7, 8, 10-五氧化苯并[c]菲那喹类生物碱cheilutine（8）和sanguilutine（18），其原料为相应的2, 3, 7, 8-四氧化苯并[c]菲那喹。
• New findings in Bischler-Napieralski reaction: Formation of 12-azonianaphth[1. 2-b]azulenes from 2-aryl-1-naphthylformamides and their unexpected transformation into benz[g]indoles through hydride reduction
  作者：Tsutomu Ishikawa、Tatsuru Saito、Shigeru Noguchi、Hisashi Ishii、Shuichiro Ito、Tadashi Hata

  DOI：10.1016/0040-4039(95)00399-w

  日期：1995.4

  The Bischler-Napieralski Reaction (BNR) of N-[2-(2-alkoxy-4, 5-methylenedioxyphenyl)-1-naphthyl]-N-methylformamides using POCl3 abnormally gave 12-azonianaphth[1. 2-b]azulene derivatives, which could be effectively transformed into benz[g]indoles with a 1-alkoxy-8-oxabicyclo[3. 2. 1]oct-2-ene skeleton through hydride reduction, as additional cyclized products. In contrast, the BNR of naphthylformamides

  使用POCl 3的N- [2-（2-烷氧基-4，5-亚甲基二氧苯基）-1-萘基] -N-甲基甲酰胺的Bischler-Napieralski反应（BNR）异常生成12-氮杂萘并[1]。2- b ] azulene衍生物，可以有效地转化为带有1-烷氧基-8-氧杂双环[3]的苯并[ g ]吲哚。2. 1]通过氢化物还原的辛-2-烯骨架，作为另外的环化产物。相反，在苯环的相同位置具有甲氧基取代亚甲二氧基官能团的萘甲酰胺的BNR导致正常环化，定量得到苯并[ c ]菲啶鎓氯化物。将讨论异常BNR和吲哚形成的推测机制。
• [EN] QUATERNARY ALKALOID DERIVATIVES OF CHELIDONIUM MAJUS L<br/>[FR] DERIVES ALCALOIDES QUATERNAIRES DE CHELIDONIUM MAJUS L
  申请人：NOWICKY WASSILI

  公开号：WO2006032380A1

  公开（公告）日：2006-03-30

  The invention relates to alkaloid reaction products obtainable in a process wherein alkaloids are reacted with a derivatizing agent, preferably thiotepa or another one of the compounds listed in Fig.3, whereafter unreacted derivatizing agent and other water-soluble compounds are removed from the reaction mixture by washing with water or a suitable aqueous solvent, whereafter the reaction mixture is subjected to a treatment with strong acid, preferably hydrogen chloride (HCI), to precipitate a water soluble salt of the reaction products. The precipitated reaction products comprise at least one quaternary alkaloid derivative and are suitable as drugs for prophylactic or therapeutic application, particularly in the treatment of immunological or metabolic dysfunctions, and cancer.

  本发明涉及一种碱性物质反应产物，该产物可以在一种过程中获得，该过程中碱性物质与衍生化试剂（优选为硫唑磷或图3中列出的其他化合物之一）反应，然后通过用水或适当的水溶性溶剂洗涤来去除未反应的衍生化试剂和其他水溶性化合物，然后将反应混合物用强酸（优选为盐酸）处理，以沉淀反应产物的水溶性盐。沉淀的反应产物包括至少一种季铵碱衍生物，适用于预防或治疗应用的药物，特别是在免疫或代谢功能障碍和癌症的治疗中。
• Structural Studies of Chelirubine and Chelilutine Free Bases
  作者：Jiří Dostál、Jiří Slavík、Milan Potáček、Radek Marek、Otakar Humpa、Vladimír Sklenář、Jaromír Toušek、Edmond de Hoffmann、Raoul Rozenberg

  DOI：10.1135/cccc19981045

  日期：——

  The structures of chelirubine and chelilutine free bases have been examined by 2D NMR spectroscopy and mass spectrometry. Chelirubine chloride (1a) upon treatment with Na₂CO₃ yielded free base which possessed the constitution of bis(5,6-dihydrochelirubin-6-yl) ether (2a). The free base of chelilutine (1b) was determined to be bis(5,6-dihydrochelilutin-6-yl) ether (2b). The aqueous NH₃ treatment of chelilutine (1b) produced bis(5,6-dihydrochelilutin-6-yl)amine (3b). 6-Hydroxy-5,6-dihydrochelirubine (4a) and 6-hydroxy-5,6-dihydrochelilutine (4b) were detected only in CDCl₃ solution by NMR spectroscopy. In CDCl₃, the compound 2b underwent hydrolysis to 4b that was immediately followed by the reverse condensation to a diastereomer of 2b. Pseudokinetics of this reaction was followed by NMR spectroscopy and quantum chemical calculations were carried out to support the suggested type of molecular symmetry alteration. The known alkaloid dihydrochelirubine (5) was isolated for the first time from Sanguinaria canadensis.

  自由碱的结构已通过2D NMR光谱和质谱进行了检查。氯化钡鲁宾（1a）经Na2CO3处理后产生的自由碱具有双(5,6-二氢鲁宾-6-基)醚（2a）的构成。鲁宾碱（1b）的自由碱被确定为双(5,6-二氢鲁宾碱-6-基)醚（2b）。鲁宾碱（1b）的水溶性NH3处理产生了双(5,6-二氢鲁宾碱-6-基)胺（3b）。6-羟基-5,6-二氢鲁宾（4a）和6-羟基-5,6-二氢鲁宾碱（4b）只在CDCl3溶液中通过NMR光谱检测到。在CDCl3中，化合物2b经水解生成4b，紧接着发生了反向缩合形成2b的对映异构体。通过NMR光谱跟踪了该反应的伪动力学，并进行了量子化学计算以支持所建议的分子对称性改变类型。已知生物碱二氢鲁宾（5）首次从加拿大血根中分离出来。
• Drug delivery devices
  申请人：VIPONT PHARMACEUTICAL, INC.

  公开号：EP0297535A2

  公开（公告）日：1989-01-04

  Drug delivery devices and techniques are described for use in treatment of periodontal disease and the like. The delivery device includes benzo (c) phenanthridine alkaloid in a bioerodable and biocompatible material. The alkaloid is slowly released from the bioerodable material in the oral cavity. The bioerodable material may be polymeric and may be natural or synthetic. The delivery device may be inserted subgingivally (e.g., in a periodontal pocket) where the alkaloid is released slowly over a period of days.

  描述了用于治疗牙周病等的给药装置和技术。这种给药装置将苯并(c)菲啶生物碱装在生物可吸收材料和生物相容性材料中。生物碱从口腔中的生物可吸收材料中缓慢释放出来。可生物降解的材料可以是聚合材料，也可以是天然或合成材料。给药装置可插入龈下（如牙周袋内），生物碱在数天内缓慢释放。