Geneserin | 34021-37-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: Geneserin
• 英文别名: (4aS)-2,4a,9-trimethyl-6-methylcarbamoyloxy-(4ar,9ac)-2,3,4,4a,9,9a-hexahydro-[1,2]oxazino[6,5-b]indole；1,2-Oxazino[6,5-b]indol-6-ol, 2,3,4,4a,9,9a-hexahydro-2,4a,9-trimethyl-, methylcarbamate, (4aS-cis)-；(2,4a,9-trimethyl-4,9a-dihydro-3H-oxazino[6,5-b]indol-6-yl) N-methylcarbamate
• CAS: 34021-37-9
• 化学式: C₁₅H₂₁N₃O₃
• 分子量: 291.35
• InChiKey: CNBHDDBNEKKMJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  54
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-<2-(N-hydroxy-N-methylamino)ethyl>-1,3-dimethyl-5-(N-methylcarbamoyloxy)indol-2-(3H)-one 以75%的产率得到
  参考文献：
  名称：

  SHISHIDO, KOZO;HIROYA, KOU;KOMATSU, HIRONORI;FUKUMOTO, KEIICHIRO;KAMETANI+, J. CHEM. SOC. PERKIN TRANS., 1,(1987) N 11, 2491-2495

  摘要：

  DOI：

文献信息

• Nitric Oxide Releasing Prodrugs of Therapeutic Agents
  申请人：SATYAM Apparao

  公开号：US20110263526A1

  公开（公告）日：2011-10-27

  The present invention relates to nitric oxide releasing prodrugs of known drugs or therapeutic agents which are represented herein as compounds of formula (I) wherein the drugs or therapeutic agents contain one or more functional groups independently selected from a carboxylic acid, an amino, a hydroxyl and a sulfhydryl group. The invention also relates to processes for the preparation of the nitric oxide releasing prodrugs (the compounds of formula (I)), to pharmaceutical compositions containing them and to methods of using the prodrugs.

  本发明涉及已知药物或治疗剂的一氧化氮释放前药，其在此处表示为式(I)的化合物，其中药物或治疗剂包含一个或多个功能基团，独立地选自羧酸、氨基、羟基和巯基。该发明还涉及制备一氧化氮释放前药（式(I)的化合物）的方法，含有它们的药物组合物以及使用这些前药的方法。
• Technology for the Preparation of Microparticles
  申请人：Malakhov Michael

  公开号：US20090098207A1

  公开（公告）日：2009-04-16

  Microspheres are produced by contacting a solution of a macromolecule or small molecule in a solvent with an antisolvent and a counterion, and chilling the solution. The microspheres are useful for preparing pharmaceuticals, nutraceuticals, cosmetic products and the like of defined dimensions.

  微球是通过将溶液中的大分子或小分子与抗溶剂和对离子接触，并冷却溶液而制备的。这些微球可用于制备具有明确定义尺寸的药物、营养保健品、化妆品等产品。
• Carbamoyl esters that inhibit cholinesterase and release pharmacologically active agents
  申请人：Verheijen C. Jeroen

  公开号：US20050096387A1

  公开（公告）日：2005-05-05

  Carbamoyl esters inhibit cholinesterase activity and, upon hydrolysis release a pharmacologically active agent. In one embodiment, the carbamoyl ester has the following structure: wherein A is selected from the group consisting of an unsubstituted aryl, a substituted aryl, an unsubstituted heteroaryl and a substituted heteroaryl. The carbamoyl esters are employed in methods to treat an individual. The pharmacologically active agent obtained by hydrolysis of the carbamoyl esters can treat, for example, a nervous system condition, a cholinergic deficiency and conditions or diseases associated with a deficiency in a pharmacologically active agent, such as acetylcholine.

  碳酰基酯抑制胆碱酯酶活性，水解后释放出药理活性成分。在一种实施例中，碳酰基酯具有以下结构：其中A选自无取代芳基、取代芳基、无取代杂环芳基和取代杂环芳基的群组。碳酰基酯用于治疗个体的方法中。通过水解碳酰基酯获得的药理活性成分可以治疗例如神经系统疾病、胆碱能缺乏以及与药理活性成分缺乏相关的疾病或病症，例如乙酰胆碱。
• Nitrate prodrugs able to release nitric oxide in a controlled and selective way and their use for prevention and treatment of inflammatory, ischemic and proliferative diseases
  申请人：Scaramuzzino, Giovanni

  公开号：EP1336602A1

  公开（公告）日：2003-08-20

  New pharmaceutical compounds of general formula (I): F-(X)q where q is an integer from 1 to 5, preferably 1; -F is chosen among drugs described in the text, -X is chosen among 4 groups -M, -T, -V and -Y as described in the text. The compounds of general formula (I) are nitrate prodrugs which can release nitric oxide in vivo in a controlled and selective way and without hypotensive side effects and for this reason they are useful for the preparation of medicines for prevention and treatment of inflammatory, ischemic, degenerative and proliferative diseases of musculoskeletal, tegumental, respiratory, gastrointestinal, genito-urinary and central nervous systems.

  通式（I）的新药物化合物：F-（X）q，其中q是1到5的整数，最好是1；-F是在文本中描述的药物中选择的，-X是在文本中描述的4个组-M，-T，-V和-Y中选择的。通式（I）的化合物是硝酸盐前药，可以在体内以受控和选择性的方式释放一氧化氮，而不会产生降压副作用，因此它们非常适用于制备用于预防和治疗肌肉骨骼，皮肤，呼吸，消化，泌尿和中枢神经系统的炎症，缺血，退行性和增生性疾病的药物。
• [EN] A PROCESS FOR THE PREPARATION OF AMINOCARBONYL DERIVATIVES OF GENESEROLINE HAVING SELECTIVE BRAIN ANTICHOLINESTERASE ACTIVITY<br/>[FR] PROCEDE DE PREPARATION DE DERIVES AMINOCARBONYLE DE GENESEROLINE AYANT UNE ACTIVITE ANTICOLINESTERASE SELECTIVE DANS LE CERVEAU
  申请人：CHIESI FARMACEUTICI S.P.A.

  公开号：WO1999019329A1

  公开（公告）日：1999-04-22

  (EN) A process for the preparation of compounds of formula (I), wherein R is C2-C20 linear or branched alkyl, C3-C7 cycloalkyl, phenyl or benzyl, which can optionally be substituted by C1-C4 alkyl, halogen or C1-C4 alkoxy group, said process comprising: a) oxidation of eserine with hydrogen peroxide in the presence of a base and subsequent hydrolysis to geneseroline, without isolating the intermediate geneserine; b) acylation of geneseroline with an isocyanate of formula R-N=C=O, wherein R is as defined above, in the presence of a basic catalyst; c) optional transformation into a pharmaceutically acceptable salt. Compounds of formula (I) wherein R is a phenyl or benzyl, which can be optionally substituted by alkyl, halogen or alkoxy, are selective, potent brain anticholinesterase inhibitors.(FR) On décrit un procédé de préparation de composés de formule (I). Dans la formule, R représente alkyle C2-C1 linéaire ou ramifié, cycloalkyle C3-C7, phényle ou benzyle qui peut être facultativement substitué par alkyle C1-C4, halogène ou groupe alcoxy C1-C4. Le procédé consiste: a) à oxyder de l'ésérine avec du peroxyde d'hydrogène en présence d'une base puis à effectuer l'hydrolyse subséquente en généséroline, sans isoler la génésérine intermédiaire; b) à acyler la généséroline avec un isocyanate de formule R-N=C=O, R étant tel que décrit ci-dessus, en présence d'un catalyseur basique; c) à transformer facultativement le produit obtenu en un sel pharmaceutiquement acceptable. Les composés de formule (I) dans laquelle R représente phényle ou benzyle, pouvant être facultativement substitués par alkyle, halogène ou alcoxy sont de puissants inhibiteurs anticolinestérases sélectifs dans le cerveau.

  一种制备式(I)化合物的方法，其中R为C2-C20线性或支链烷基，C3-C7环烷基，苯基或苄基，可以选择性地被C1-C4烷基，卤素或C1-C4烷氧基取代，该方法包括：a)在碱的存在下，用过氧化氢氧化酯酶生成基因酯碱，然后水解成基因酯碱，而不分离中间体基因酯；b)在碱性催化剂的存在下，用式R-N=C=O的异氰酸酯对基因酯碱进行酰化反应，其中R如上所述；c)可选地将其转化为药学上可接受的盐。其中R为苯基或苄基，可以选择性地被烷基，卤素或烷氧基取代的式(I)化合物是选择性、强效的脑部抗胆碱酯酶抑制剂。

表征谱图