6-ethynyl-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene | 119362-54-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 6-ethynyl-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene
• 英文别名: 1,1,4,4-Tetramethyl-6-ethynyl-1,2,3,4-tetrahydronaphthalene；6-ethynyl-1,1,4,4-tetramethyl-2,3-dihydronaphthalene
• CAS: 119362-54-8
• 化学式: C₁₆H₂₀
• 分子量: 212.335
• InChiKey: HROQNFYTUDZWBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  6-ethynyl-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene 在 盐酸 、 正丁基锂 、 1,2-双(二苯基膦)乙烷氯化镍 、 水 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 10.84h， 生成 芳维甲酸
  参考文献：
  名称：

  Synthesis of arotinoid acid and temarotene using mixed (Z)-1,2-bis(organylchalcogene)-1-alkene as precursor

  摘要：

  An efficient and novel total synthesis of the two bioactive retinoids temarotene and arotinoid acid (TTNPB) is described. The key steps in this process include the regio and stereoselective hydrotelluration of thioacetylene 9 and Te/Li transmetalation of mixed (Z)-1,2-bis(organylchalcogene)-1-alkene (Z)-3. The subsequent reaction involving the beta-phenylthio vinyl lithiated intermediate 10 with dimethyl sulfate gave the (E)-vinyl sulfide 11. The Ni+2 cross-coupling of 11 with the corresponding phenylzinc bromide and p-oxazoline phenylzinc bromide 12 afforded the respective temarotene 2 and retinoid-oxazoline substituted 13. Finally, compound 13 was deprotected with HCl to furnish arotinoid acid (TTNPB) 1. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.07.092
• 作为产物：
  描述：

  6-iodo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 水 、 三乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 乙醚 为溶剂， 生成 6-ethynyl-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene
  参考文献：
  名称：

  [EN] SYNTHETIC RETINOIDS FOR CONTROL OF CELL DIFFERENTIATION
  [FR] RÉTINOÏDES SYNTHÉTIQUES POUR LE CONTRÔLE DE LA DIFFÉRENCIATION DES CELLULES

  摘要：

  本发明涉及式(I)的合成视黄酸化合物及其在控制细胞分化或凋亡方面的应用。

  公开号：

  WO2012076842A1

文献信息

• General Synthesis of Retinoids and Arotinoids via Palladium-Catalyzed Cross-Coupling of Boronic Acids with Electrophiles
  作者：Alicia Torrado、Susana López、Rosana Alvarez、Angel R. de Lera

  DOI：10.1055/s-1995-3905

  日期：1995.3

  A novel approach to the synthesis of retinoids and arotinoids (including heterocyclic analogs) is described which is based on the thallium-accelerated palladium-catalyzed cross-coupling of boronic acids with a variety of electrophiles (the Suzuki reaction).

  本文介绍了一种制备类视黄醇和阿洛视黄醇（包括杂环类似物）的新方法，该方法基于铊促进的钯催化下硼酸与多种亲电试剂的交叉偶联合成反应（Suzuki反应）。
• Design and biological evaluation of synthetic retinoids: probing length vs. stability vs. activity
  作者：Graeme Clemens、Kevin R. Flower、Peter Gardner、Andrew P. Henderson、Jonathan P. Knowles、Todd B. Marder、Andrew Whiting、Stefan Przyborski

  DOI：10.1039/c3mb70273a

  日期：——

  All trans-retinoic acid (ATRA) is widely used to direct the differentiation of cultured stem cells. When exposed to the pluripotent human embryonal carcinoma (EC) stem cell line, TERA2.cl.SP12, ATRA induces ectoderm differentiation and the formation of neuronal cell types. We report in this study that novel polyene chain length analogues of ATRA require a specific chain length to elicit a biological responses of the EC cells TERA2.cl.SP12, with synthetic retinoid AH61 being particularly active, and indeed more so than ATRA. The impacts of both the synthetic retinoid AH61 and natural ATRA on the TERA2.cl.SP12 cells were directly compared using both RT-PCR and Fourier Transform Infrared Micro-Spectroscopy (FT-IRMS) coupled with multivariate analysis. Analytical results produced from this study also confirmed that the synthetic retinoid AH61 had biological activity comparable or greater than that of ATRA. In addition to this, AH61 has the added advantage of greater compound stability than ATRA, therefore, avoiding issues of oxidation or decomposition during use with embryonic stem cells.

  全反式视黄酸（ATRA）广泛用于指导培养的干细胞分化。当暴露于多能性人胚胎癌（EC）干细胞系TERA2.cl.SP12时，ATRA诱导外胚层分化和神经细胞类型的形成。本研究报告了新型多烯链长类似物ATRA需要特定的链长才能引起EC细胞TERA2.cl.SP12的生物学反应，其中合成视黄酸AH61特别活跃，实际上比ATRA更活跃。通过RT-PCR和傅里叶变换红外显微光谱（FT-IRMS）结合多元分析，直接比较了合成视黄酸AH61和天然ATRA对TERA2.cl.SP12细胞的影响。本研究的分析结果也证实，合成视黄酸AH61具有与ATRA相当或更高的生物活性。此外，AH61相对于ATRA具有化合物稳定性更高的优势，因此在使用过程中避免了氧化或分解的问题。
• Design, Synthesis and Anticancer Biological Evaluation of Novel 1,4-Diaryl- 1,2,3-triazole Retinoid Analogues of Tamibarotene (AM80)
  作者：Mariana Aleixo、Taís Garcia、Diego Carvalho、Luiz Viana、Marcos Amaral、Najla Kassab、Marilin Cunha、Indiara Pereira、Palimécio Guerrero Jr.、Renata Perdomo、Maria Matos、Adriano Baroni

  DOI：10.21577/0103-5053.20170119

  日期：——

  We report herein the design and synthesis via click chemistry of twelve novel triazole retinoid analogues of tamibarotene (AM80) and the evaluation of their anticancer activities against six cancer cell lines: HL60, K562, 786, HT29, MCF7 and PC3. Among the synthesized compounds, two were more potent than tamibarotene against solid tumor cells, and one of them had similar potency to tamibarotene against

  我们在这里报告的设计和合成通过点击化学的十二种新的他米巴罗汀（AM80）的三唑类视黄醇类似物及其对六种癌细胞系（HL60，K562、786，HT29，MCF7和PC3）的抗癌活性的评估。在合成的化合物中，有两种对实体瘤细胞的功效比他米巴罗汀强，其中一种对HL60细胞的功效与他米巴罗汀相似。这项工作中报道的类维生素A药他米巴罗汀（AM80）中酰胺基团与1,2,3-三唑核之间的生物立体交换是产生有用的抗癌化合物的有效策略。
• Synthesis and evaluation of synthetic retinoid derivatives as inducers of stem cell differentiation
  作者：Victoria B. Christie、Jonathan H. Barnard、Andrei S. Batsanov、Caroline E. Bridgens、Emily B. Cartmell、Jonathan C. Collings、Daniel J. Maltman、Christopher P. F. Redfern、Todd B. Marder、Stefan Przyborski、Andrew Whiting

  DOI：10.1039/b808574a

  日期：——

  subsequently its biological activity. To address this source of variability, synthetic retinoid analogues have been designed and synthesised that retain stability during use and maintain biological function in comparison to ATRA. It is also shown that subtle modifications to the structure of the synthetic retinoid compound impacts significantly on biological activity, as when exposed to cultured human pluripotent

  全反式维甲酸（ATRA）及其相关类似物是神经系统发育过程中细胞分化和功能的重要介体。众所周知，ATRA可以诱导人多能干细胞分化为神经组织。然而，并不总是意识到，ATRA在溶液中时高度易受异构化的影响，这会影响ATRA的有效浓度并进而影响其生物学活性。为了解决这种可变性的来源，已经设计并合成了合成类维生素A类似物，与ATRA相比，它们在使用过程中保持稳定性并保持生物学功能。还表明，对合成类维生素A化合物的结构进行细微修饰会显着影响其生物活性，当暴露于培养的人多能干细胞时，合成类维生素A 4-（5,5,8,8-四甲基-5,6,7,8-四氢萘-2-基乙炔基）苯甲酸4a（对位异构体）诱导神经分化类似于ATRA。相反，暴露于合成类视黄醇3-（5,5,8,8-四甲基-5,6,7,8-四氢萘-2-基乙炔基）苯甲酸4b（元异构体）的干细胞产生的神经元很少。和大量的上皮样细胞。用于此类合成类维生素A化合物的
• INHIBITORS OF SPHINGOSINE KINASE
  申请人：Stieber Frank

  公开号：US20120252815A1

  公开（公告）日：2012-10-04

  The present invention relates to compounds of the formula (I), in which R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , M 1 , M 2 , M 3 , Y 1 , Y 2 , V, W, n, m and o have the gleanings given herein, and physiologically acceptable salts, derivatives, prodrugs, solvates, tautomers and stereoisomers thereof, including mixtures thereof in all ratios, for use in the treatment of diseases which are influenced by inhibition of Sph kinase 1.

  本发明涉及化合物的结构式(I)，其中R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14、R15、R16、R17、M1、M2、M3、Y1、Y2、V、W、n、m和o具有此处所述的含义，以及其生理上可接受的盐、衍生物、前药、溶剂化合物、互变异构体和立体异构体，包括所有比例的混合物，用于治疗受Sph激酶1抑制影响的疾病。