6-(aminomethyl)-N,N-dimethylnaphthalen-2-amine | 1004549-15-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-(aminomethyl)-N,N-dimethylnaphthalen-2-amine
• 英文别名: (6-(aminomethyl)naphthalen-2-yl)-dimethylamine
• CAS: 1004549-15-8
• 化学式: C₁₃H₁₆N₂
• 分子量: 200.283
• InChiKey: DGYJEJFZXRAHCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(dimethylamino)-6-naphthonitrile 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以10%的产率得到6-(aminomethyl)-N,N-dimethylnaphthalen-2-amine
  参考文献：
  名称：

  基于MAO-A特异性双光子荧光探针的分子内电荷转移增强策略用于神经胶质瘤细胞/组织成像

  摘要：

  MAO-A 促进人神经胶质瘤细胞的增殖。在此，我们报告了一系列基于分子内电荷转移增强策略的 MAO-A 特异性双光子小分子荧光探针 ( A1-5 )。内源性 MAO-A 的活性可以通过双光子荧光显微镜使用A3作为代表探针在不同的生物样品中进行选择性成像，包括人神经胶质瘤细胞/组织。该研究为神经胶质瘤的视觉检测提供了新的工具。

  DOI：

  10.1039/d1cc04744b

文献信息

• FLUORESCENT SUBSTRATES FOR MONOAMINE TRANSPORTERS AS OPTICAL FALSE NEUROTRANSMITTERS
  申请人：of New York The Trustees of Columbia University in the City

  公开号：US20130190497A1

  公开（公告）日：2013-07-25

  The present invention relates to compounds of the general structure: wherein Y is O, X is O, bond α is absent and bond β is present, or Y is H, X is CH, bond α is present, and bond β is absent; atom Z is a carbon and bonds χ, δ and γ are present, or is a nitrogen and bonds χ, δ and γ are absent; R 1 is —H, —OH, —O—R 7 , —N(H)—R 8 , —N(H)—(CH 2 ) n —NH 2 , —N(R 9 )(R 10 ), or a piperazine cation; R 2 is either covalently bound to R 9 , or is —H, or is covalently bound to R 3 so as to form a substituted or unsubstituted pyrrole or R 2 is covalently bound to R 9 or R 8 or R 7 ; or R 1 and R 2 are covalently joined to form an aromatic ring; R 3 is either covalently bound to R 2 so as to form a pyrrole, or is, inter alia, —H, —OH, alkyl, or when Z is nitrogen R 3 is ═O; R 4 is, inter alia, —H, —OH, or —R 11 NH 2 ; R 5 is, inter alia, —H, —OH, or —R 12 NH 2 , and R 6 is either is covalently bound to R 10 or is —H, or R 6 is covalently bound to R 10 or R 8 or R 7 . This invention also provides processes for making the compounds as well as methods for monitoring activity of monoamine transporters or treating monoamine transporter-associated diseases by employing the compounds.

  本发明涉及以下通用结构的化合物：其中Y为O，X为O，键α不存在，键β存在，或Y为H，X为CH，键α存在，键β不存在；原子Z为碳并存在键χ，δ和γ，或为氮并不存在键χ，δ和γ；R1为—H，—OH，—O—R7，—N(H)—R8，—N(H)—(CH2)n—NH2，—N(R9)(R10)，或哌嗪阳离子；R2要么与R9共价结合，要么为—H，要么与R3共价结合以形成取代或未取代的吡咯，或R2与R9或R8或R7共价结合；或R1和R2共价结合以形成芳香环；R3要么与R2共价结合以形成吡咯，要么为—H，—OH，烷基，或者当Z为氮时，R3为═O；R4为—H，—OH，或—R11NH2；R5为—H，—OH，或—R12NH2，R6要么与R10共价结合，要么为—H，要么与R10或R8或R7共价结合。本发明还提供制备这些化合物的方法以及利用这些化合物监测单胺转运体活性或治疗单胺转运体相关疾病的方法。
• [EN] FLUORESCENT SUBSTRATES FOR MONOAMINE TRANSPORTERS AS OPTICAL FALSE NEUROTRANSMITTERS<br/>[FR] SUBSTRATS FLUORESCENTS DE TRANSPORTEURS DE MONOAMINES EN TANT QUE FAUX NEUROTRANSMETTEURS OPTIQUES
  申请人：UNIV COLUMBIA

  公开号：WO2008013997A2

  公开（公告）日：2008-01-31

  [EN] The present invention relates to compounds of the general structure: wherein Y is O, X is O, bond a is absent and bond ß is present, or Y is H, X is CH, bond a is present, and bond ß is absent; atom Z is a carbon and bonds ?, d and ? are present, or is a nitrogen and bonds ?, d and ? are absent; R₁ is -H, -OH, -O-R₇, -N(H) -R₈, -N (H) - (CH₂) _n-NH₂, -N(R₉) (R₁₀), or a piperazine cation; R₂ is either covalently bound to R₉, or is -H, or is covalently bound to R₃ so as to form a substituted or unsubstituted pyrrole or R₂ is covalently bound to R₉ or R₈ or R₇; or R₁ and R₂ are covalently joined to form an aromatic ring; R₃ is either covalently bound to R₂ so as to form a pyrrole, or is, inter alia, -H, -OH, alkyl, or when Z is nitrogen R₃ is =O; R₄ is, inter alia, -H, -OH, or -R₁₁NH₂; R₅ is, inter alia, -H, -OH, or -R₁₂NH₂, and R₆ is either is covalently bound to R₁₀ or is -H, or R₆ is covalently bound to R₁₀ or R₈ or R₇. This invention also provides processes for making the compounds as well as methods for monitoring activity of monoamine transporters or treating monoamine transporter-associated diseases by employing the compounds.
  [FR] L'invention porte sur des composés de formule générale (I) dans laquelle: Y est O, X est O, la liaison a est absente et la liaison ß est présente, ou Y est H, X est CH, la liaison a est présente, et la liaison ß est absent; l'atome Z est un carbone et les liaisons ?, d et ? sont présente, ou est azote et les liaisons ?, d et ? sont absentes; R1 est -H, -OH, -O-R7, -N(H) -R8, -N (H) - (CH2) n-NH2, -N(R9) (R10), ou un cation de pipérazine; R2 est soit lié par covalence à R9, ou est -H, ou est lié par covalence à R3 pour former un pyrrole substitué ou non substitué, ou R2 lié par covalence à R9 ou R8 ou R7; ou R1 et R2 sont liés par covalence pour former un cycle aromatique; R3 est soit lié par covalence à R2 former un pyrrole, ou est, entre autres, -H, -OH, alkyle, ou si Z est azote R3 est = O; R4 est, entre autres, -H, -OH, ou -R11NH2; R5 est, entre autres, -H, -OH, ou -R12NH2, et R6 est soit lié par covalence à R10 ou est -H, ou R6 est lié par covalence à R10 ou R8 ou R7. L'invention porte également sur le procédé d'élaboration desdits composés et sur des méthodes de surveillance de l'activité de transporteurs de monoamines, ou sur des méthodes de traitement de maladies associées aux transporteurs de monoamines par utilisation desdits composés.
• Intramolecular charge transfer enhancing strategy based MAO-A specific two-photon fluorescent probes for glioma cell/tissue imaging
  作者：Haixiao Fang、Riri Shi、Ding Chen、Yunwei Qu、Qiong Wu、Xuekang Yang、Xiaomei Lu、Cheng-Wu Zhang、Lin Li、Kah-Leong Lim

  DOI：10.1039/d1cc04744b

  日期：——

  fluorescent probes (A1–5) based on an intramolecular charge transfer enhancing strategy. The activity of endogenous MAO-A can be selectively imaged using A3 as a representative probe in different biological samples including human glioma cells/tissues via two-photon fluorescence microscopy. The study provides new tools for the visual detection of glioma.

  MAO-A 促进人神经胶质瘤细胞的增殖。在此，我们报告了一系列基于分子内电荷转移增强策略的 MAO-A 特异性双光子小分子荧光探针 ( A1-5 )。内源性 MAO-A 的活性可以通过双光子荧光显微镜使用A3作为代表探针在不同的生物样品中进行选择性成像，包括人神经胶质瘤细胞/组织。该研究为神经胶质瘤的视觉检测提供了新的工具。