2-hydroxy-4-(1-piperidinyl)benzaldehyde | 96649-21-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 2-hydroxy-4-(1-piperidinyl)benzaldehyde
• 英文别名: 2-hydroxy-4-(piperidin-1-yl)benzaldehyde；2-Hydroxy-4-piperidin-1-ylbenzaldehyde
• CAS: 96649-21-7
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: ZQTOHLJISJWVKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-hydroxy-4-(1-piperidinyl)benzaldehyde 在 硫酸 作用下， 以 四氢呋喃 为溶剂， 反应 27.0h， 生成
  参考文献：
  名称：

  一种近红外的高量子产率染料及其制备与应 用

  摘要：

  本发明公开了一种新型近红外的高量子产率染料，该染料具有如下结构式I：R1、R2、R6、R7分别独立的为氢、低级烃基、醚基、取代烷基或酰基；R3、R4、R5、R8、R9、R10分别独立的为氢、低级烃基或卤素；R11为氢、甲基、氰基、或三氟甲基；为阴离子；还公开了该染料的制备方法。该染料具有良好的生物相容性、低毒性、较长的荧光发射和很高的荧光量子产率，避免了背景自发荧光，可获得高信噪比的荧光成像图，用于生物体系中核仁RNA荧光标记，对研究与核仁RNA相关的生理学过程有着重要的作用。

  公开号：

  CN107141840B
• 作为产物：
  描述：

  3-哌啶基苯酚 在 四甲基乙二胺 、 仲丁基锂 、 sodium hydride 作用下， 反应 9.25h， 生成 2-hydroxy-4-(1-piperidinyl)benzaldehyde
  参考文献：
  名称：

  Effect of different dialkylamino groups on the regioselectivity of lithiation of O-protected 3-(dialkylamino)phenols

  摘要：

  DOI：

  10.1021/jo00215a020

文献信息

• [EN] INHIBITORS OF CYSTATHIONINE BETA SYNTHASE TO REDUCE THE NEUROTOXIC OVERPRODUCTION OF ENDOGENOUS HYDROGEN SULFIDE<br/>[FR] INHIBITEURS DE LA CYSTATHIONINE BÊTA SYNTHASE UTILISABLES EN VUE DE LA RÉDUCTION DE LA SURPRODUCTION NEUROTOXIQUE DE SULFURE D'HYDROGÈNE ENDOGÈNE
  申请人：FOND JEROME LEJEUNE

  公开号：WO2013068592A1

  公开（公告）日：2013-05-16

  The invention is directed to inhibitors of cystathionine beta synthase which, among other biochemical effects, allow reduction of the neurotoxic overproduction of endogenous hydrogen sulphide. These compounds and pharmaceutical compositions containing them are useful for the prevention and treatment of cognitive disorders such as cognitive disorders in Down syndrome. The invention also relates to methods for preventing or treating cognitive disorders including cognitive disorders in Down Syndrome.

  本发明涉及胱硫醚β合酶抑制剂，除其他生化作用外，还允许减少内源性硫化氢的神经毒性过度产生。这些化合物以及含有它们的药物组合物对于预防治疗认知障碍，如下氏综合症中的认知障碍等是有用的。本发明还涉及用于预防或治疗认知障碍的方法，包括下氏综合症中的认知障碍。
• COMPOUNDS FOR TREATING SPINAL MUSCULAR ATROPHY
  申请人：PTC Therapeutics Inc.

  公开号：US20150119380A1

  公开（公告）日：2015-04-30

  Provided herein are compounds, compositions thereof and uses therewith for treating spinal muscular atrophy. In a specific embodiment, provided herein are compounds of a form that may be used to modulate the inclusion of exon 7 of SMN2 into mRNA that is transcribed from the SMN2 gene. In another specific embodiment, provided herein are compounds of a form that may be used to modulate the inclusion of exon 7 of SMN1 into mRNA that is transcribed from the SMN1 gene. In yet another embodiment, provided herein are compounds of a form that may be used to modulate the inclusion of exon 7 of SMN1 and SMN2 into mRNA that is transcribed from the SMN1 and SMN2 genes, respectively.

  本文提供了用于治疗脊髓性肌萎缩症的化合物、其组合物及与其一起使用的用途。在一个具体实施例中，本文提供了一种可以用来调节SMN2基因转录的mRNA中包含外显子7的形式化合物。在另一个具体实施例中，本文提供了一种可以用来调节SMN1基因转录的mRNA中包含外显子7的形式化合物。在另一个实施例中，本文提供了一种可以用来调节SMN1和SMN2基因转录的mRNA中包含外显子7的形式化合物。
• Spirodipyrane und ihre Verwendung als Farbbildner für Kopierverfahren
  申请人：BASF Aktiengesellschaft

  公开号：EP0010740A1

  公开（公告）日：1980-05-14

  Farbbildner der allgemeinen Formel in der A der Rest eines ankondensierten Benzol- oder 2,1-Naphthalinrings, wobei beide Reste durch C1- bis C4-Alkyl, C1- bis C4-Alkoxy, Nitro, Chlor, Brom oder C1- bis C6-Alkoxycarbonyl sein können; R1 C1- bis C16-Alkyl, C2- bis C10-Phenylalkyl oder gegebenenfalls durch C1- bis C4-Alkyl, C1- bis C4-Alkoxy, Chlor oder Brom substituiertes Phenyl; und R2 und R3 unabhängig von einander Wasserstoff, C1- bis C12-Alkyl, durch Cyan, Chlor, Methoxy oder Äthoxy substituiertes C2- bis C4-Alkyl, C5- bis C7-Cycloalkyl, C7- bis C10-Phenylalkyl, oder gegebenenfalls durch 1 bis 3 Methyl substituiertes und an das in 6- und/oder 8-Stellung befindliche C-Atom des Benzrings gebundenes Trimethylen oder R2 C1- bis C4-Alkyl und R3 gegebenenfalls durch Chlor, Brom, C1- bis C3-Alkyl, Methoxy oder Äthoxy substituiertes Phenyl oder R2 Benzyl und R3 β-Cyanäthyl oder -Moroholinvl. Pvrrolidinvl. N'-C1- bis C4-Alkylpi- perazinyl oder Isoindolinyl bedeuten. Die Verbindungen (I) geben in Kontakt mit Elektroacceptoren violette, blaue bis grüne Färbungen, während auf nicht beschichtetem Papier praktisch keine Farbbildung eintritt. Die Verbindungen (I) eignen sich als Farbbildner für druckempfindliche Aufzeichnungs- oder Kopiermaterialien.

  前者的通式为 其中 A 是融合在一起的苯环或 2，1-萘环的基，这两个基可以是 C1-C4-烷基、C1-C4-烷氧基、硝基、氯、溴或 C1-C6- 烷氧基羰基；R1 是 C1-C16- 烷基、C2-C10-苯基烷基或未被取代或被 C1-C4- 烷基、C1-C4-烷氧基、氯或溴取代的苯基；R2 和 R3 独立地为氢、C1-至 C12-烷基、被氰基、氯、甲氧基或乙氧基取代的 C2-至 C4-烷基、C5-至 C7-环烷基、C7-至 C10-苯基烷基、或 R2 C1-至 C4-烷基和 R3苯基任选被氯、溴、C1-至 C3-烷基、甲氧基或乙氧基取代，或 R2 苄基和 R3 β-氰乙基或-Moroholinvl。 -N'-C1-至 C4-烷基高嗪基或异吲哚啉基。 化合物（I）在与电受体接触时会呈现出紫色、蓝色和绿色，而在未涂布的纸张上几乎不会形成颜色。 化合物 (I) 适合用作压敏记录或复印材料的显色剂。
• Discovery and Optimization of Small Molecule Splicing Modifiers of Survival Motor Neuron 2 as a Treatment for Spinal Muscular Atrophy
  作者：Matthew G. Woll、Hongyan Qi、Anthony Turpoff、Nanjing Zhang、Xiaoyan Zhang、Guangming Chen、Chunshi Li、Song Huang、Tianle Yang、Young-Choon Moon、Chang-Sun Lee、Soongyu Choi、Neil G. Almstead、Nikolai A. Naryshkin、Amal Dakka、Jana Narasimhan、Vijayalakshmi Gabbeta、Ellen Welch、Xin Zhao、Nicole Risher、Josephine Sheedy、Marla Weetall、Gary M. Karp

  DOI：10.1021/acs.jmedchem.6b00460

  日期：2016.7.14

  The underlying cause of spinal muscular atrophy (SMA) is a deficiency of the survival motor neuron (SMN) protein. Starting from hits identified in a high-throughput screening campaign and through structure activity relationship investigations, we have developed small molecules that potently shift the alternative splicing of the SMN2 exon 7, resulting in increased production of the full-length SMN mRNA and protein. Three novel chemical series, represented by compounds 9, 14, and 20, have been optimized to increase the level of SMN protein by >50% in SMA patient-derived fibroblasts at concentrations of <160 nM. Daily administration of these compounds to severe SMA Delta 7 mice results in an increased production of SMN protein in disease-relevant tissues and a significant increase in median survival time in a dose-dependent manner. Our work supports the development of an orally administered small molecule for the treatment of patients with SMA.
• Synthesis and pharmacological evaluation of carboxycoumarins as a new antitumor treatment targeting lactate transport in cancer cells
  作者：Nihed Draoui、Olivier Schicke、Antony Fernandes、Xavier Drozak、Fady Nahra、Amélie Dumont、Jonathan Douxfils、Emmanuel Hermans、Jean-Michel Dogné、Romu Corbau、Arnaud Marchand、Patrick Chaltin、Pierre Sonveaux、Olivier Feron、Olivier Riant

  DOI：10.1016/j.bmc.2013.09.010

  日期：2013.11

  Under hypoxia, cancer cells consume glucose and release lactate at a high rate. Lactate was recently documented to be recaptured by oxygenated cancer cells to fuel the TCA cycle and thereby to support tumor growth. Monocarboxylate transporters (MCT) are the main lactate carriers and therefore represent potential therapeutic targets to limit cancer progression. In this study, we have developed and implemented a stepwise in vitro screening procedure on human cancer cells to identify new potent MCT inhibitors. Various 7-substituted carboxycoumarins and quinolinone derivatives were synthesized and pharmacologically evaluated. Most active compounds were obtained using a palladium-catalyzed Buchwald-Hartwig type coupling reaction, which proved to be a quick and efficient method to obtain aminocarboxycoumarin derivatives. Inhibition of lactate flux revealed that the most active compound 19 (IC50 11 nM) was three log orders more active than the CHC reference compound. Comparison with warfarin, a conventional anticoagulant coumarin, further showed that compound 19 did not influence the prothrombin time which, together with a good in vitro ADME profile, supports the potential of this new family of compounds to act as anticancer drugs through inhibition of lactate flux. (C) 2013 Elsevier Ltd. All rights reserved.

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