(+/-)-mappicine | 54352-77-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (+/-)-mappicine
• 英文别名: R,S-mappicine；mappicine；7-(1-hydroxy-propyl)-8-methyl-11H-indolizino[1,2-b]quinolin-9-one；(+/-)-7-(1-hydroxypropyl)-8-methylindolizino[1,2-b]quinolin-9(11H)-one；7-(1-hydroxypropyl)-8-methylindolizino[1,2-b]quinolin-9(11H)-one；(+/-)-Mappicin；7-(1-hydroxypropyl)-8-methyl-11H-indolizino[1,2-b]quinolin-9-one
• CAS: 54352-77-1
• 化学式: C₁₉H₁₈N₂O₂
• 分子量: 306.364
• InChiKey: WSXJPXFVULHYMX-UHFFFAOYSA-N

物化性质

• 熔点：
  267.4 °C
• 沸点：
  616.0±55.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  53.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-mappicine 在 phosphate buffer 、 lipase Amano PS (Pseudomonas cepacia) 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 72.0h， 生成 (S)-mappicine acetate
  参考文献：
  名称：

  Enantioselective synthesis of (S)- and (R)-mappicines and their analogues

  摘要：

  The naturally occurring alkaloids, camptothecin and mappicine ketone were converted to racemic mappicine acetate which was enantioselectively hydrolyzed to (S)- and (R)-mappicines in high optical purity using baker's yeast and a lipase, Amano PS. Treatment of the racemic acetate with baker's yeast afforded (S)-mappicine while with Amano PS yielded (R)-mappicine. 9-Methoxycamptothecin and 9-methoxymappicine ketone underwent similar conversion to (S)- and (R)-9-methxymappicines. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00397-x
• 作为产物：
  描述：

  1,3-二氢吡咯并[3,4-b]喹啉-2-羧酸乙酯 在 palladium dihydroxide 吡啶 、 氢气 、 sodium methylate 、 sodium acetate 作用下， 以 甲醇 、 乙醇 、 溶剂黄146 、 乙腈 为溶剂， 反应 66.0h， 生成 (+/-)-mappicine
  参考文献：
  名称：

  收敛的全合成甲氧苄啶酮：领先的抗病毒化合物

  摘要：

  描述了天然存在的马卡比汀酮1和马卡比汀2的有效的全合成。该方法基于三环胺5与假酰氯20的组装。利用弗里德兰德缩合法来构建ABC骨架，并使用过选择性的Diels-Alder方法来制备假酰氯。

  DOI：

  10.1016/s0040-4020(99)00191-x

文献信息

• [EN] CRYSTALLINE FORM II OF 7-(DIMETHOXY-METHYL) CAMPTOTHECIN, ITS USE AS INTERMEDIATE AND PRODUCTS OBTAINED THEREFROM<br/>[FR] FORME CRISTALLINE II DE LA 7-(DIMÉTHOXY-MÉTHYL)CAMPTOTHÉCINE, SON UTILISATION COMME INTERMÉDIAIRE ET PRODUITS OBTENUS À PARTIR DE CELLE-CI
  申请人：SIGMA TAU IND FARMACEUTI

  公开号：WO2009016068A1

  公开（公告）日：2009-02-05

  This invention relates to a process for preparing a crystalline form of (4S)-11-(dimethoxymethyl)-4-ethyl-4-hydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]qui-no line-3,14(4H,12H)-dione (also named 7-(dimethoxy-methyl)camptothecin). With the provision of a particular crystallization step, in appropriate way, a new crystalline form of the above compound is obtained. The process for the preparation of the polymorph Form II comprises transforming camptothecin to the corresponding 7-(dimethoxy-methyl)-camptothecin, and crystallizing it from methanol.

  这项发明涉及一种制备(4S)-11-(二甲氧甲基)-4-乙基-4-羟基-1H-吡喃并[3',4':6,7]吲哚并[1,2-b]喹诺啉-3,14(4H,12H)-二酮（又名7-(二甲氧甲基)喜树碱）的晶型的方法。通过提供特定的结晶步骤，以适当的方式，得到了上述化合物的新晶型。制备多形式II的方法包括将喜树碱转化为相应的7-(二甲氧甲基)-喜树碱，并从甲醇中结晶化。
• [EN] PREPARATION OF LABELLED COMPOUNDS<br/>[FR] PRÉPARATION DE COMPOSÉS MARQUÉS
  申请人：ISIS INNOVATION

  公开号：WO2010133851A1

  公开（公告）日：2010-11-25

  The invention relates to a process for producing a labelled compound, which process comprises treating a compound of formula (I), wherein X is a moiety to be labelled or a detectable label, and R1, R2, R3 and R4 are substitutent groups as defined herein; with a compound of formula (II) : N3-L-Y (π) wherein Y is a detectable label or a moiety to be labelled, provided that if X in the compound of formula (I) is a moiety to be labelled, then Y is a detectable label and if X in the compound of formula (I) is a detectable label, then Y is a moiety to be labelled; and L is a bond or a linking group, thereby producing a labelled compound of formula (IH) by Staudinger Ligation. Groups R3 and R4 may comprise fluorous moieties, in order to facilitate purification of the labelled compound of formula (IH). The invention also provides methods of imaging a human or non-human patient or a cell or in vitro sample, using the labelled compound of formula (III) thus produced, as well as imaging methods in which the compounds of formulae (I) and (II) are administered to the patient, cell or sample. The invention further provides novel compounds of formula (I) and formula (III), a process for producing the compounds of formula (T), and a combination product for medical imaging comprising a compound of formula (I) and a compound of formula (II).

  该发明涉及一种用于生产标记化合物的方法，该方法包括处理具有以下结构式（I）的化合物，其中X是待标记的基团或可检测的标记，R1、R2、R3和R4是如本文所定义的取代基团；与具有以下结构式（II）的化合物：N3-L-Y（π），其中Y是可检测的标记或待标记的基团，前提是如果结构式（I）中的X是待标记的基团，则Y是可检测的标记，如果结构式（I）中的X是可检测的标记，则Y是待标记的基团；L是键合或连接基团，从而通过斯陶丁格反应生成具有结构式（IH）的标记化合物。取代基团R3和R4可能包括氟基团，以便促进对具有结构式（IH）的标记化合物的纯化。该发明还提供了使用因此生产的具有结构式（III）的标记化合物对人类或非人类患者、细胞或体外样本进行成像的方法，以及在这些方法中向患者、细胞或样本施用结构式（I）和（II）化合物的成像方法。该发明还提供了具有结构式（I）和结构式（III）的新化合物，以及生产结构式（T）化合物的方法和包含结构式（I）化合物和结构式（II）化合物的医学成像组合产品。
• Total synthesis of nothapodytine B and (±)-mappicine
  作者：Subhash P. Chavan、Rasapalli Sivappa

  DOI：10.1016/j.tetlet.2004.03.089

  日期：2004.5

  A novel, efficient total synthesis of the naturally occurring antiviral nothapodytine B (2, mappicine ketone) is reported. The approach is based on the successful implementation of the Johnson orthoester rearrangement of allylic alcohol 7 for assembly of a pyridone D ring precursor with the necessary functionalities. Nothapodytine B is converted into mappicine 3 by NaBH4 reduction.

  报道了一种新颖，有效的全天然合成的抗病毒非亲和素B（2，Mappicine酮）的合成方法。该方法基于成功实现烯丙基醇7的约翰逊原酸酯重排，以组装具有必要功能性的吡啶酮D环前体。通过NaBH 4还原，将非苦参碱B转化为马皮甜碱3。
• Synthesis of (+/-) mappicine and mappicine ketone
  作者：Kevin E. Henegar、Ted A. Baughman

  DOI：10.1002/jhet.5570400407

  日期：2003.7

  Mappicine and mappicine ketone are camptothecin analogs of interest as antiviral agents. A novel synthesis of these compounds is described using a Friedlander condensation. The requisite ketone is prepared via a regioselective ortho-directed metallation/alkylation of a trisubstituted pyridine. This is condensed with N-t-butyloxycarbonyl-o-aminobenzaldehyde as a convenient, stable o-aminobenzaldehyde

  Mappicine和Mappicine酮是喜树碱类似物的抗病毒剂。使用Friedlander缩合描述了这些化合物的新合成方法。必要的酮是通过三取代吡啶的区域选择性邻位定向金属化/烷基化制备的。将其与Nt-丁氧基羰基-邻氨基苯甲醛缩合，作为弗里德兰德缩合反应中方便，稳定的邻氨基苯甲醛当量。
• Substituted indolizino\x9b1,2-b!quinolinones
  申请人：SmithKline Beecham Corporation

  公开号：US05883255A1

  公开（公告）日：1999-03-16

  The present invention provides a method of treating viral infections by using antiviral substituted indolizino\x9b1,2-b!quinolinone compounds, antiviral substituted indolizino\x9b1,2-b!quinolinone compounds, and pharmaceutical compositions thereof.

  本发明提供了一种使用抗病毒取代的吲哚嗪并[1,2-b]喹啉酮化合物、抗病毒取代的吲哚嗪并[1,2-b]喹啉酮化合物以及其制成的药物组合物治疗病毒感染的方法。