2-Methylpapaverinium iodide | 2679-26-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 2-Methylpapaverinium iodide
• 英文别名: 1-(3',4'-dimethoxybenzyl)-6,7-dimethoxy-2-methylisoquinolinium iodide；1-(3,4-Dimethoxybenzyl)-6,7-dimethoxy-2-methylisochinolinium-iodid；6,7-dimethoxy-2-methyl-1-veratryl-isoquinolinium; iodide；6,7-Dimethoxy-2-methyl-1-veratryl-isochinolinium; Jodid；Papaverin-methojodid；1-((3,4-Dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methylisoquinolinium iodide；1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methylisoquinolin-2-ium;iodide
• CAS: 2679-26-7
• 化学式: C₂₁H₂₄NO₄*I
• 分子量: 481.33
• InChiKey: NEDMOWXPUGKQAV-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.29
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  40.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-Methylpapaverinium iodide 在 lithium aluminium tetrahydride 、 乙醚 作用下， 生成 1,2-dihydro-2-methylpapaverine
  参考文献：
  名称：

  ReduktionenQuartärercyclischer铵盐和氢化铝锂

  摘要：

  Es wird gezeigt，Dss sichquartäreCyclische Ammoniumsalze，Chinolin oder Isochinolin alsGrundkörper能力，Durch锂铝氢化物zu o-Dihydroderivaten reduzieren lassen。Diese Methode帽子，Gegenüberder klassischen Reduktionsmethode derartiger Verbindungen mit Natriumdithionit，Gewisse Vorteile。

  DOI：

  10.1002/hlca.19490320340
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氢碘酸 作用下， 生成 2-Methylpapaverinium iodide
  参考文献：
  名称：

  Decker; Klauser, Chemische Berichte, 1904, vol. 37, p. 529

  摘要：

  DOI：

文献信息

• Simple Isoquinoline and Benzylisoquinoline Alkaloids as Potential Antimicrobial, Antimalarial, Cytotoxic, and Anti-HIV Agents
  作者：Kinuko Iwasa、Masataka Moriyasu、Yoko Tachibana、Hye-Sook Kim、Yusuke Wataya、Wolfgang Wiegrebe、Kenneth F Bastow、L.Mark Cosentino、Mutsuo Kozuka、Kuo-Hsiung Lee

  DOI：10.1016/s0968-0896(01)00154-7

  日期：2001.11

  Twenty-six simple isoquinolines and 21 benzylisoquinolines were tested for antimicrobial, antimalarial, cytotoxic, and anti-HIV activities. Some simple isoquinoline alkaloids were significantly active in each assay, and may be useful as lead compounds for developing potential chemotherapeutic agents. These compounds include 13 (antimicrobial), 25, 26, and 42 (antimalarial), 13 and 25 (cytotoxic), and

  测试了26种简单异喹啉和21种苄基异喹啉的抗微生物，抗疟疾，细胞毒性和抗HIV活性。一些简单的异喹啉生物碱在每种测定法中均具有显着活性，并且可用作开发潜在化学治疗剂的先导化合物。这些化合物包括13（抗微生物），25、26和42（抗动物），13和25（细胞毒性）以及28和29（抗HIV）。异喹啉或二氢异喹啉鎓类型的季氮原子可能有助于提高前三种活性的效力。相反，发现四氢异喹啉盐和6,7-二羟基异喹啉盐具有抗HIV活性。
• Pseudobase formation in 2-methylpapaverinium cations and their biotransformation by enzymes of rat liver homogenates in vitro
  作者：Daniela Walterová、Vladimír Preininger、Ladislav Dolejš、František Grambal、Miroslav Kyselý、Ivo Válka、Vilím Šimánek

  DOI：10.1135/cccc19800956

  日期：——

  2-Methylpapaverinium iodide (I), 2'-hydroxymethyl-2-methylpapaverinium iodide (IX), and 2-methyl-3,4-dihydropapaverinium iodide (X. CH₃I) form pseudobase by addition of hydroxide ions to the C(1)=N⁽⁺⁾ bond. 2'-Hydroxymethyl-2-methyl-3,4-dihydropapaverinium iodide (XV) and 2'-hydroxymethyl-2-methyl-9-oxo-3,4-dihydropapaverinium iodide (XVI) react with hydroxide ions in aqueous medium under formation of cyclic pseudobases XVII and XVIII. The equilibrium constants (K_R+) of pseudobase formation have been measured in aqueous ethanol (1 : 1 w/w, 25°C, ionic strength 0.1). The quaternary papaverinium derivatives are metabolized to isoquinilones and carbonyl compounds by means of rat liver enzymes. The role of pseudobases in these biotransformations has been discussed and biogenetic conclusions have been drawn.

  2-甲基罂粟碱碘化物（I），2'-羟甲基-2-甲基罂粟碱碘化物（IX），和2-甲基-3,4-二氢罂粟碱碘化物（X. CH3I）通过将氢氧根离子加到C(1)=N(+)键形成伪碱基。2'-羟甲基-2-甲基-3,4-二氢罂粟碱碘化物（XV）和2'-羟甲基-2-甲基-9-氧代-3,4-二氢罂粟碱碘化物（XVI）在水性介质中与氢氧根离子反应，形成环状伪碱基XVII和XVIII。在水性乙醇（1：1 w/w，25°C，离子强度0.1）中测定了伪碱基形成的平衡常数（KR+）。季铵罂粟碱衍生物通过大鼠肝酶代谢为异喹啉酮和羰基化合物。讨论了伪碱基在这些生物转化中的作用，并得出了生物合成的结论。
• Biotransformation of Phenolic 1-Benzyl-<i>N</i>-methyltetrahydroisoquinolines in Plant Cell Cultures Followed by LC/NMR, LC/MS, and LC/CD
  作者：Wenhua Cui、Kinuko Iwasa、Makiko Sugiura、Atsuko Takeuchi、Chisato Tode、Yumi Nishiyama、Masataka Moriyasu、Harukuni Tokuda、Kazuyoshi Takeda

  DOI：10.1021/np068060r

  日期：2007.11.1

  (+/-)-1-Benzyl-N-methyltetrahydroisoquinolines 7-10 and 11-14 with one and two hydroxy groups on the aromatic rings, respectively, were fed individually to cultured cells of Corydalis and Macleaya species, respectively. The structures of the metabolites were determined by using combinatorial techniques, including LC/NMR, LC/MS-MS, and LC/CD. The enantiomeric excesses of the metabolites were derived from LC/CD and LC/MS-MS analyses. In cell cultures of Corydalis and Macleaya species, laudanine (7), with a hydroxy group at C-3', can form the berberine bridge at C-2' and C-6' to produce S- and R-enantiomers of 2,3,9,10- and 2,3,10,11-oxygenated protoberberines (20 and 21), respectively, whereas reticuline (11) and protosinomenine (12), incoporating a hydroxy group at C-3', form the berberine bridge at C-2' to furnish the S-enantiomer of 2,3,9,10-oxygenated protoberberines (23 and 21), respectively.

  (±)-1-苄基-N-甲基四氢异喹啉类化合物（7-10 和 11-14），分别在芳香环上具有一个和两个羟基基团，被单独单独分别喂养了 CORS和 MAC细胞培养物。代谢物的结构通过组合技术确定，包括 LC/NMR、LC/MS-MS 和 LC/CD。代谢物的对映体过量通过 LC/CD 和 LC/MS-MS 分析得出。在 CORS和 MAC物种的细胞培养中，羟基位于 C-3' 的 Laudanine（7）可在 C-2' 和 C-6' 处形成小檗碱桥，分别产生 2,3,9,10- 和 2,3,10,11- 氧化的原小檗碱的 S-和 R-对映体（20 和 21），而羟基位于 C-3'的Reticuline（11）和Protosinomenine（12），分别在 C-2' 处形成小檗碱桥，提供 2,3,9,10- 氧化原小檗碱的 S-对映体（23 和 21）。
• Reaktionen von Isochinolinium-Salzen mit Hydroxylamin-Derivaten, 3. Mitteilung. Mechanismus der Aminoxid-Bildung / Reactions of Isoquinolinium Salts with Hydroxylamine Derivatives, 3rd Communication. Mechanism of Amine Oxide Generation
  作者：H. Möhrle、R. Nießen

  DOI：10.1515/znb-1999-0715

  日期：1999.7.1

  2-Methylpapaverinium iodide (1) reacted with hydroxylamine to papaverine-N-oxide (2), but without a detectable intermediate and only in moderate yield, caused by the steric hindrance of the 1-substituent. The ring opened product of 2-dinitrophenylisoquinolinium salt with hydroxylamine, the enamine-oxime 3b gave rise to a 3-substituted cyclic nitrone (6), when heated with triethylamine. This alkali-stable compound was transformed with acid quantitatively to isoquinoline-N-oxide (4). The enaminonitrile 9c, treated with triethylamine showed cyclization to the iminoisoquinoline 10, which by loss of nitrous acid produced the tetracyclic azaindole 11. The 2-methoxyisoquinolinium salt 16 was cleaved with O-methylhydroxylamine to the resistant di(O-methyloximes) (20a/b), unable to form the amine oxide 4. From these and former results, a mechanism for the ring opening of cycliminium salts and the recyclization to amine oxides was proposed.

  2-甲基罂粟碱碘化物（1）与羟胺反应生成罂粟碱-N-氧化物（2），但没有可检测的中间体，且仅产生中等收率，这是由于1-取代基的立体位阻所致。2-二硝基苯基异喹啉盐与羟胺反应生成环打开产物，烯胺-肟3b在与三乙胺加热后生成3-取代的环状亚硝基（6）。这种碱稳定的化合物经酸转化定量生成异喹啉-N-氧化物（4）。烯胺腈9c与三乙胺处理后环化生成亚胺异喹啉10，通过失去亚硝酸生成四环氮吲哚11。2-甲氧基异喹啉盐16经O-甲基羟胺裂解生成抗性的二（O-甲氧肟）（20a/b），无法形成胺氧化物4。根据这些和以往的结果，提出了环戊铵盐环打开和再环化为胺氧化物的机理。
• Flow Conditions‐Controlled Divergent Oxidative Cyclization of Reticuline‐Type Alkaloids to Aporphine and Morphinandienone Natural Products
  作者：Bi Bali Judicaël Tra、Abollé Abollé、Vincent Coeffard、François‐Xavier Felpin

  DOI：10.1002/ejoc.202200301

  日期：2022.6.13

  We describe a divergent continuous-flow approach for the biomimetic oxidative cyclization of reticuline-type alkaloids to aporphine and morphinandienone natural products using hypervalent iodine compounds.

  我们描述了一种使用高价碘化合物将网状生物碱仿生氧化环化为阿吗啡和吗啡二烯酮天然产物的发散连续流动方法。