2-(1,1-dicyano-1-propen-2-yl)-6-(dimethylamino)naphthalene | 178385-38-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(1,1-dicyano-1-propen-2-yl)-6-(dimethylamino)naphthalene
• 英文别名: 1,1-dicyano-2-((6-dimethylamino)naphthalene-2-yl)propene；1,1-dicyano-2-[6-(dimethylamino)naphthalen-2-yl]propene；DDNP；2-(1,1-dicyanopropen-2-yl)-6-dimethylaminonaphthalene；2-(1-[6-(Dimethylamino)-2-naphthyl]ethylidene)malononitrile；2-[1-[6-(dimethylamino)naphthalen-2-yl]ethylidene]propanedinitrile
• CAS: 178385-38-1
• 化学式: C₁₇H₁₅N₃
• 分子量: 261.326
• InChiKey: OGQSKUQBPUTFHS-UHFFFAOYSA-N

物化性质

• 沸点：
  452.3±35.0 °C(Predicted)
• 密度：
  1.159±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  50.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1,1-dicyano-1-propen-2-yl)-6-(dimethylamino)naphthalene 在 silica 、 氯仿 作用下， 以 N,N-二甲基甲酰胺二甲基缩醛 为溶剂， 反应 16.0h， 以to give 2-{(2E)-3-(dimethylamino)-1-[6-(dimethylamino)-2-naphthyl]-2-propenylidene}-malononitrile (1.19 g, 98%)的产率得到2-{(2E)-3-(dimethylamino)-1-[6-(dimethylamino)-2-naphthyl]-2-propenylidene}malononitrile
  参考文献：
  名称：

  Methods for binding agents to b-amyloid plaques

  摘要：

  提供了一种用于标记体内或体外结构，例如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，最好是放射性标记以便通过正电子发射断层扫描（PET）进行检测。

  公开号：

  US20070053831A1
• 作为产物：
  描述：

  6-甲氧基-2-乙酰萘 在 吡啶 、 六甲基磷酰三胺 、 lithium 作用下， 反应 40.5h， 生成 2-(1,1-dicyano-1-propen-2-yl)-6-(dimethylamino)naphthalene
  参考文献：
  名称：

  1,1-Dicyano-2-[6-(dimethylamino)naphthalen-2-yl]propene (DDNP):  A Solvent Polarity and Viscosity Sensitive Fluorophore for Fluorescence Microscopy

  摘要：

  1,1-Dicyano-2-[6-(dimethylamino)naphthalen-2=yl]propene (II, DDNP) has been synthesized as a fluorescent dye whose intramolecular rotational relaxation is solvent polarity and viscosity dependent. Its fluorescence emission (lambda max: 470-610 nm in hydrophobic and viscous environments) is in a very favorable region for its use with visible fluorescence microscopy, without interference from cell or tissue autofluorescence. Its fluorescence emission quantum yield in an aqueous environment is very low, allowing for facile differentiation between lipid or protein bound state and aqueous media. II crystallizes into two solid isoforms containing one (red crystals) and two conformers (yellow crystals), exhibiting differing spectral properties. X-ray crystal structures reveal a planar arrangement between dimethylamino and naphthalenyl moieties, with out-of-plane arrangements between the malononitrile and naphthalene ring found in each of the three conformers.

  DOI：

  10.1021/ja9543356

文献信息

• Dicyanovinylnaphthalenes for neuroimaging of amyloids and relationships of electronic structures and geometries to binding affinities
  作者：Andrej Petrič、Scott A. Johnson、Hung V. Pham、Ying Li、Simon Čeh、Amalija Golobič、Eric D. Agdeppa、Gerald Timbol、Jie Liu、Gyochang Keum、Nagichettiar Satyamurthy、Vladimir Kepe、Kendall N. Houk、Jorge R. Barrio

  DOI：10.1073/pnas.1214134109

  日期：2012.10.9

  binding affinities. The extreme cases were a nonplanar analog t-butyl-FDDNP, which shows low binding affinity for Abeta aggregates (520 nM K(i)) in vitro and a nearly planar tricyclic analog cDDNP, which displayed the highest binding affinity (10 pM K(i)). Using a previously published X-ray crystallographic model of 1,1-dicyano-2-[6-(dimethylamino)naphthalen-2-yl]propene (DDNP) bound to an amyloidogenic

  正电子发射断层扫描 (PET) 探针 2-(1-[6-[(2-氟乙基)(甲基)氨基]-2-萘基]亚乙基) (FDDNP) 用于淀粉样蛋白-β 的无创脑成像。 Abeta) 和其他淀粉样蛋白聚集体存在于阿尔茨海默病和其他神经退行性疾病中。使用光谱和计算方法合成和表征了一系列 FDDNP 类似物。这些分子的结合亲和力已通过实验测量并通过使用计算模型进行解释。这些类似物是通过系统地修改 FDDNP 的供体和受体侧来创建的，以了解与 Abeta 聚合体的最佳结合的结构要求。FDDNP 及其类似物是中性的、环境敏感的、具有高偶极矩的荧光分子，正如它们的光谱特性和偶极矩计算所证明的那样。这些化合物的优选溶液状态构象与结合亲和力直接相关。极端情况是非平面类似物 t-丁基-FDDNP，其在体外对 Abeta 聚集体 (520 nM K(i)) 显示出低结合亲和力，而近乎平面的三环类似物 cDDNP，显示出最高结合亲和力
• [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。
• High throughput method for functionally classifying proteins identified using a genomics approach
  申请人：——

  公开号：US20020168686A1

  公开（公告）日：2002-11-14

  The present invention provides a method for functionally classifying a protein that is capable of unfolding due to a thermal change. The method comprises screening one or more of a multiplicity of different molecules for their ability to shift the thermal unfolding curve of the protein, wherein a shift in the thermal unfolding curve indicates that the molecule binds to the protein or affects the stability in a measurable way; generating an activity spectrum for the protein wherein the activity spectrum reflects a set of molecules, from the multiplicity of molecules, that shift the thermal unfolding curve, of the protein and therefore are ligands that bind to the protein, comparing the activity spectrum for the protein to one or more functional reference spectrum lists; and classifying the protein according to the set of molecules in the multiplicity of different molecules that shift the thermal unfolding curve of the protein.

  本发明提供了一种功能分类能够由于热变化而发生展开的蛋白质的方法。该方法包括筛选一种或多种不同分子的多重组合，以检测它们移动蛋白质的热展开曲线的能力，其中热展开曲线的移动表示该分子结合到蛋白质或以可测量的方式影响其稳定性；生成蛋白质的活性谱，其中活性谱反映了从多重分子中移动蛋白质的热展开曲线的分子集，因此是结合到蛋白质的配体；将蛋白质的活性谱与一个或多个功能参考谱列表进行比较；并根据多种不同分子的集合将蛋白质进行分类，这些分子移动蛋白质的热展开曲线。
• 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。