乙烯二氧基螺哌隆 | 54080-21-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 乙烯二氧基螺哌隆
• 英文名称: 1-phenyl-8-[3-(2-(4-fluorophenyl)-1,3-dioxolan-2-yl)propyl]-1,3,8-triazaspiro[4.5]decan-4-one
• 英文别名: 8-<3-<2-(4-fluorophenyl)-1,3-dioxolan-2-yl>propyl>-1-phenyl-1,3,8-triazaspiro<4.5>decan-4-one；8-{3-[2-(4-fluoro-phenyl)-[1,3]dioxolan-2-yl]-propyl}-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one；1,3,8-Triazaspiro(4.5)decan-4-one, 8-(3-(2-(p-fluorophenyl)-1,3-dioxolan-2-yl)propyl)-1-phenyl-；8-[3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one
• CAS: 54080-21-6
• 化学式: C₂₅H₃₀FN₃O₃
• 分子量: 439.53
• InChiKey: SFQUTTGZLHJZLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  54
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙烯二氧基螺哌隆 在 盐酸 、 sodium hydride 作用下， 以 乙醇 为溶剂， 反应 18.33h， 生成 3-Butyl-8-[4-(4-fluoro-phenyl)-4-oxo-butyl]-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one
  参考文献：
  名称：

  Effect of N-alkylation on the affinities of analogs of spiperone for dopamine D2 and serotonin 5-HT2 receptors

  摘要：

  Two series of N-substituted spiperone analogues were prepared and evaluated in vitro to measure their affinities for dopamine D2 and serotonin 5-HT2 receptors. Substitution of the amide nitrogen with an alkyl group of five carbon units or less resulted in analogues displaying a low selectivity for D2 compared to 5-HT2 receptors. However, a moderate improvement in selectivity for D2 receptors was observed with N-benzylspiperone. Substitution at either the ortho or para position of the benzyl group resulted in a further reduction in affinity for 5-HT2 receptors and improvement in the selectivity ratio. Examination of N-substituted analogues of spiperone may provide insights into the topography of the antagonist binding region of the 5-HT2 receptor. The results also suggest that an F-18-labeled analogue of N-(4-nitrobenzyl)spiperone (4p) may be a suitable tracer for studying D2 receptors with positron emission tomography since this compound displays a high selectivity for D2 receptors relative to that of spiperone and N-methylspiperone.

  DOI：

  10.1021/jm00081a002
• 作为产物：
  描述：

  1-苯基-1,3,8-三唑螺环(4,5)十烷-4-酮 、 2-(3-氯丙基)-2-(4-氟苯基)-1,3-二氧戊烷 在 potassium carbonate 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以82%的产率得到乙烯二氧基螺哌隆
  参考文献：
  名称：

  Khorana, Nantaka; Bondarev, Mikhail; Dukat, Malgorzata, Medicinal Chemistry Research, 1999, vol. 9, # 9, p. 657 - 667

  摘要：

  DOI：

文献信息

• Methods for binding agents to b-amyloid plaques
  申请人：Barrio R. Jorge

  公开号：US20070053831A1

  公开（公告）日：2007-03-08

  A method for labeling structures, such as β-amyloid plaques and neurofibrillary tangles, in vivo or in vitro, is provided and comprises contacting brain tissue with one or more compounds, preferably radiolabeled for detection by positron emission tomography (PET).

  提供了一种用于在体内或体外标记结构（如β-淀粉样斑块和神经原纤维缠结）的方法，包括将大脑组织与一个或多个化合物接触，最好是用正电子发射断层扫描（PET）检测的放射性标记。
• [EN] METHODS FOR LABELING beta -AMYLOID PLAQUES AND NEUROFIBRILLARY TANGLES<br/>[FR] PROCEDE DE MARQUAGE POUR PLAQUES BETA-AMYLOIDE ET DEGENERESCENCE NEUROFIBRILLAIRE
  申请人：UNIV CALIFORNIA

  公开号：WO2000010614A1

  公开（公告）日：2000-03-02

  A method for labeling β-amyloid plaques and neurofibrillary tangles in vivo and in vitro, comprises contacting a compound of formula (I) with mammalian tissue. In formula (I), R1 is selected from the group consisting of -C(O)-alkyl, -C(O)-alkylenyl-R4, -C(O)O-alkyl, -C(O)O-alkylenyl-R4, -C=C(CN)2-alkyl, -C=C(CN)2-alkylenyl-R4, (a), (b) and (c); R4 is a radical selected from the group consisting of alkyl, substituted alkyl, aryl and substituted aryl; R5 is a radical selected from the group consisting of -NH2, -OH, -SH, -NH-alkyl, -NHR4, -NH-alkylenyl-R4, -O-alkyl, -O-alkylenyl-R4, -S-alkyl, and S-alkylenyl-R4; R6 is a radical selected from the group consisting of -CN, -COOH, -C(O)O-alkyl, -C(O)O-alkylenyl-R4, -C(O)alkyl, -C(O)-alkylenyl-R4, -C(O)-halogen, -C(O)NH2 -C(O)NH-alkyl, -C(O)NH-alkylenyl-R4; R7 is a radical selected from the group consisting of O, NH, and S; and R8 is N, O or S. R2 and R3 are each independently selected from the group consisting of alkyl and alkylenyl-R10, wherein R10 is selected from the group consisting of -OH, -OTs, halogen, spiperone, spiperone ketal and spiperone-3-yl. Alternatively, R2 and R3 together form a heterocyclic ring, optionally substituted with at least one radical selected from the group consisting of alkyl, alkoxy, OH, OTs, halogen, alkylenyl-R10, carbonyl, spiperone, spiperone ketal and spiperone-3-yl. In the compounds of formula (I), one or more of the hydrogen, halogen or carbon atoms can, optionally, be replaced with a radiolabel.

  一种用于体内和体外标记β淀粉样斑块和神经原纤维缠结的方法，包括将式(I)的化合物与哺乳动物组织接触。在式(I)中，R1选自由-C(O)-烷基、-C(O)-亚烷基-R4、-C(O)O-烷基、-C(O)O-亚烷基-R4、-C=C(CN)2-烷基、-C=C(CN)2-亚烷基-R4、(a)、(b)和(c)的群；R4是选自烷基、取代烷基、芳基和取代芳基的基团；R5是选自-NH2、-OH、-SH、-NH-烷基、-NHR4、-NH-亚烷基-R4、-O-烷基、-O-亚烷基-R4、-S-烷基和-S-亚烷基-R4的基团；R6是选自-CN、-COOH、-C(O)O-烷基、-C(O)O-亚烷基-R4、-C(O)烷基、-C(O)-亚烷基-R4、-C(O)-卤素、-C(O)NH2、-C(O)NH-烷基、-C(O)NH-亚烷基-R4的基团；R7是选自O、NH和S的基团；R8是N、O或S。R2和R3各自独立地选自烷基和亚烷基-R10，其中R10选自-OH、-OTs、卤素、司匹仑、司匹仑缩醛和司匹仑-3-基。或者，R2和R3共同形成一个杂环环，可选地用至少一个选自烷基、烷氧基、OH、OTs、卤素、亚烷基-R10、羰基、司匹仑、司匹仑缩醛和司匹仑-3-基的基团取代。在式(I)的化合物中，氢、卤素或碳原子中的一个或多个可以选择性地被放射性标记所取代。
• Compositions for labeling beta-amyloid plaques and neurofibrillary tangles
  申请人：——

  公开号：US20040072371A1

  公开（公告）日：2004-04-15

  Compositions useful for labeling &bgr;-amyloid plaques and neurofibrillary tangles are provided. The compositions comprises compounds of formula (I): 1 wherein R 1 is selected from the group consisting of —C(O)-alkyl, —C(O)-alkylenyl-R 4 , —C(O)O-alkyl, —C(O)O-alkylenyl-R 4 , —C═C(CN) 2 -alkyl, —C═C(CN) 2 -alkylenyl-R 4 , 2 wherein R 4 is a radical selected from the group consisting of alkyl, substituted alkyl, aryl and substituted aryl; R 5 is a radical selected from the group consisting of —NH 2 , —OH, —SH, —NH-alkyl, —NHR 4 , —NH-alkylenyl-R 4 , —O-alkyl, —O-alkylenyl-R 4 , —S-alkyl, and —S-alkylenyl-R 4 ; R 6 is a radical selected from the group consisting of —CN, —COOH, —C(O)O-alkyl, —C(O)O-alkylenyl-R 4 , —C(O)-alkyl, —C(O)-alkylenyl-R 4 , —C(O)-halogen, —C(O)NH-alkyl, —C(O)NH-alkylenyl-R 4 and —C(O)NH 2 ; R 7 is a radical selected from the group consisting of O, NH, and S; and R 8 is N, O or S; and R 2 is selected from the group consisting of alkyl and alkylenyl-R 10 and R 3 is alkylenyl-R 10 , wherein R 10 is selected from the group consisting of —OH, —OTs, halogen, spiperone, spiperone ketal, and spiperone-3-yl, or R 2 and R 3 together form a heterocyclic ring, optionally substituted with at least one radical selected from the group consisting of alkyl, alkoxy, OH, OTs, halogen, alkyl-R 10 , carbonyl, spiperone, spiperone ketal and spiperone-3-yl, and further wherein one or more of the hydrogen, halogen or carbon atoms are optionally replaced with a radiolabel.

  提供了用于标记&bgr;-淀粉样斑块和神经原纤维缠结的组合物。该组合物包括以下化合物(I)：1其中R1选自由—C(O)-烷基，—C(O)-烷基烯基-R4，—C(O)O-烷基，—C(O)O-烷基烯基-R4，—C═C(CN)2-烷基，—C═C(CN)2-烷基烯基-R4，2其中R4选自烷基，取代烷基，芳基和取代芳基中的一种基团；R5选自—NH2，—OH，—SH，—NH-烷基，—NHR4，—NH-烷基烯基-R4，—O-烷基，—O-烷基烯基-R4，—S-烷基和—S-烷基烯基-R4中的一种基团；R6选自—CN，—COOH，—C(O)O-烷基，—C(O)O-烷基烯基-R4，—C(O)-烷基，—C(O)-烷基烯基-R4，—C(O)-卤素，—C(O)NH-烷基，—C(O)NH-烷基烯基-R4和—C(O)NH2中的一种基团；R7选自O，NH和S；R8为N，O或S；R2选自烷基和烷基烯基-R10，R3为烷基烯基-R10，其中R10选自—OH，—OTs，卤素，斯皮罗隆，斯皮罗隆酮，和斯皮罗隆-3-基，或R2和R3一起形成一个杂环环，可选地取代至少一个选自烷基，烷氧基，OH，OTs，卤素，烷基-R10，羰基，斯皮罗隆，斯皮罗隆酮和斯皮罗隆-3-基的基团，进一步其中一个或多个氢，卤素或碳原子可选择用放射性标记取代。
• Methods for labeling beta-amyloid plaques and neurofibrillary tangles
  申请人：The Regents of the University of California

  公开号：US20020022002A1

  公开（公告）日：2002-02-21

  A method for labeling &bgr;-amyloid plaques and neurofibrillary tangles in vivo and in vitro, comprises contacting a compound of formula (I): 1 with mammalian tissue. In formula (I), R 1 is selected from the group consisting of —C(O)-alkyl, —C(O)-alkylenyl-R 4 , —C(O)O-alkyl, —C(O)O-alkylenyl-R 4 , —C═C(CN) 2 -alkyl, —C═C(CN) 2 -alkylenyl-R 4 , 2 R 4 is a radical selected from the group consisting of alkyl, substituted alkyl, aryl and substituted aryl; R 5 is a radical selected from the group consisting of —NH 2 , —OH, —SH, —NH-alkyl, —NHR 4 , —NH-alkylenyl-R 4 , —O-alkyl, —O-alkylenyl-R 4 , —S-alkyl, and —S-alkylenyl-R 4 ; R 6 is a radical selected from the group consisting of —CN, —COOH, —C(O)O-alkyl, —C(O)O-alkylenyl-R 4 , —C(O)-alkyl, —C(O)-alkylenyl-R 4 , —C(O)-halogen, —C(O)NH 2 , —C(O)NH-alkyl, —C(O)NH-alkylenyl-R 4 ; R 7 is a radical selected from the group consisting of O, NH, and S; and R 8 is N, O or S. R 2 and R 3 are each independently selected from the group consisting of alkyl and alkylenyl-R 10 , wherein R 10 is selected from the group consisting of —OH, —OTs, halogen, spiperone, spiperone ketal and spiperone-3-yl. Alternatively, R 2 and R 3 together form a heterocyclic ring, optionally substituted with at least one radical selected from the group consisting of alkyl, alkoxy, OH, OTs, halogen, alkylenyl-R 10 , carbonyl, spiperone, spiperone ketal and spiperone-3-yl. In the compounds of formula (I), one or more of the hydrogen, halogen or carbon atoms can, optionally, be replaced with a radiolabel.

  一种用于体内和体外标记β淀粉样斑块和神经原纤维缠结的方法，包括将式(I)的化合物1与哺乳动物组织接触。在式(I)中，R1选自由以下组成的群体：—C(O)-烷基，—C(O)-烷基亚烷基-R4，—C(O)O-烷基，—C(O)O-烷基亚烷基-R4，—C═C(CN)2-烷基，—C═C(CN)2-烷基亚烷基-R4，2R4选自由以下组成的基团：烷基，取代烷基，芳基和取代芳基；R5选自由以下组成的基团：—NH2，—OH，—SH，—NH-烷基，—NHR4，—NH-烷基亚烷基-R4，—O-烷基，—O-烷基亚烷基-R4，—S-烷基和—S-烷基亚烷基-R4；R6选自由以下组成的基团：—CN，—COOH，—C(O)O-烷基，—C(O)O-烷基亚烷基-R4，—C(O)-烷基，—C(O)-烷基亚烷基-R4，—C(O)-卤素，—C(O)NH2，—C(O)NH-烷基，—C(O)NH-烷基亚烷基-R4；R7选自由以下组成的基团：O，NH和S；R8是N，O或S。R2和R3各自独立地选自由以下组成的群体：烷基和亚烷基-R10，其中R10选自由以下组成的群体：—OH，—OTs，卤素，spiperone，spiperone ketal和spiperone-3-yl。或者，R2和R3一起形成一个杂环，可选地用以下至少一个基团取代：烷基，烷氧基，OH，OTs，卤素，亚烷基-R10，羰基，spiperone，spiperone ketal和spiperone-3-yl。在式(I)的化合物中，一个或多个氢、卤素或碳原子可以选择性地被放射性标记取代。
• NMR proof of a piperidine to pyrrolidine ring contraction during nucleophilic substitution
  作者：Gabrijela Ambrožič、Simon Čeh、Andrej Petrič

  DOI：10.1002/(sici)1097-458x(1998110)36:11<873::aid-omr375>3.0.co;2-b

  日期：1998.11

  l}‐1‐phenyl‐1,3,8‐triazaspiro[4.5] decan‐4‐one, at room and elevated temperatures were compared and the respective structure were assigned based on 1H and 13C NMR spectra. Piperidine to pyrrolidine ring transformation at elevated temperature is documented. © 1998 John Wiley & Sons, Ltd.

  1-(6-乙酰基-2-萘基)-4-[(4-甲基苯基)磺酰氧基]甲基哌啶与螺环酮缩酮8-3-[2-(4-氟苯基)-1,3反应生成的产物-dioxolan-2-yl] 丙基}-1-苯基-1,3,8-triazaspiro[4.5] decan-4-one, 在室温和高温下进行了比较，并根据 1H 和 13C NMR 光谱指定了各自的结构. 哌啶环在升高的温度下转化为吡咯烷环已被记录在案。© 1998 John Wiley & Sons, Ltd.