3,5-diiodo-4-methoxyaniline | 496801-28-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,5-diiodo-4-methoxyaniline
• 英文别名: 3.5-Dijod-p-anisidin；3,5-Dijod-4-methoxy-anilin；2.6-Dijod-4-amino-anisol
• CAS: 496801-28-6
• 化学式: C₇H₇I₂NO
• 分子量: 374.948
• InChiKey: HSUJYIOBQDIMPP-UHFFFAOYSA-N

物化性质

• 熔点：
  100 °C
• 沸点：
  412.3±45.0 °C(Predicted)
• 密度：
  2.345±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,5-diiodo-4-methoxyaniline 在 盐酸 、 乙基氯化镁 、 sodium nitrite 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 6.5h， 生成
  参考文献：
  名称：

  Increased endothelial cell selectivity of triazole-bridged dihalogenated A-ring analogues of combretastatin A–1

  摘要：

  The antiproliferative activity on ovarian cancer (SK-OV-3) cells of a series of triazole-bridged combretastatin analogues (37, 38, 40-43) containing dihalogenation of the A-ring is reported, and compared with their trimethoxy analogues (5, 15, 39). It was found that dihalogenation with either bromine or iodine was a tolerated modification when compared to the parent compound combretastatin (CA-4, 1) and had less effect than B-ring modification on potency. These compounds exhibited G(2)/M arrest, and maintained antitubulin activity. Further assays on human umbilical vein endothelial cells (HUVECs) demonstrated the potential antivascular effects of these triazoles. Of particular note was a 3,5-diiodo-4-methoxyaryl triazole (43) which had promising 7-fold selectivity for HUVECs over ovarian cancer cells. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.01.010
• 作为产物：
  描述：

  2,6-二碘-4-硝基苯酚 在 盐酸 、 tin(ll) chloride 作用下， 生成 3,5-diiodo-4-methoxyaniline
  参考文献：
  名称：

  Kalb et al., Chemische Berichte, 1926, vol. 59, p. 1864

  摘要：

  DOI：

文献信息

• The Remarkable Effect of Halogen Substitution on the Membrane Transport of Fluorescent Molecules in Living Cells
  作者：Harinarayana Ungati、Vijayakumar Govindaraj、Govindasamy Mugesh

  DOI：10.1002/anie.201804128

  日期：2018.7.16

  the plasma membrane transport in mammalian cells. The remarkably higher uptake of iodinated compounds compared to that of their chloro or bromo analogues suggests that the strong halogen bonding ability of iodine atoms may play an important role in the membrane transport. This study provides a novel strategy for the transport of fluorescent molecules across the plasma membrane in living cells.

  基于小分子的荧光探针已成为生物学中传感和成像应用的重要工具。但是，许多荧光分子的生物学应用受到低细胞摄取和高毒性的阻碍。在本文中，我们首次表明引入卤素原子可增强荧光分子的细胞吸收，并且卤素原子的性质在哺乳动物细胞的质膜运输中起着至关重要的作用。与它们的氯代或溴代类似物相比，碘代化合物的摄取显着更高，这表明碘原子的强卤素键合能力可能在膜运输中起重要作用。这项研究为活细胞中荧光分子跨质膜的运输提供了一种新的策略。
• A-Ring Dihalogenation Increases the Cellular Activity of Combretastatin-Templated Tetrazoles
  作者：Thomas M. Beale、Daniel M. Allwood、Andreas Bender、Peter J. Bond、James D. Brenton、D. Stephen Charnock-Jones、Steven V. Ley、Rebecca M. Myers、James W. Shearman、Jill Temple、Jessica Unger、Ciorsdaidh A. Watts、Jian Xian

  DOI：10.1021/ml200149g

  日期：2012.3.8

  The combretastatins have been investigated for their antimitotic and antivascular properties, and it is widely postulated that a 3,4,5-trimethoxyaryl A-ring is essential to maintain potent activity. We have synthesized new tetrazole analogues (32-34), demonstrating that 3,5-dihalogenation can consistently increase potency by up to 5-fold when compared to the equivalent trimethoxy compound on human umbilical vein endothelial cells (HUVECs) and a range of cancer cells. Moreover, this increased potency offsets that lost by installing the tetrazole bridge into combretastatin A-4 (1), giving crystalline, soluble compounds that have low nanomolar activity, arrest cells in G(2)/M phase, and retain microtubule inhibitory activity. Molecular modeling has shown that optimized packing within the binding site resulting in increased Coulombic interaction may be responsible for this improved activity.
• Genetic Population Structure and Origin of Life History Types in Chinook Salmon in British Columbia, Canada
  作者：David J. Teel、George B. Milner、Gary A. Winans、W. Stewart Grant

  DOI：10.1577/1548-8659(2000)129<0194:gpsaoo>2.0.co;2

  日期：2000.1

  We used protein electrophoresis to examine genetic population structure and origin of life history types of chinook salmon Oncorhynchus tshawytscha in British Columbia, Canada. Among 31 allozyme loci resolved in 91 samples from 63 populations of chinook salmon in rivers and hatcheries throughout British Columbia, population heterozygosities averaged 0.084 (range 0.048-0.108) and were typical of values for populations in other regions. A hierarchical gene diversity analysis indicated that 91.3% of the total allele-frequency diversity was attributable to within-population variability; the remaining 8.7% was attributable to geographic variability among populations, which was partitioned into among-river (3.3%), among-area (3.5%), and among-region (1.9%) components. Two major groups of populations appeared in the principal components analysis and in cluster analysis of genetic distances. A coastal group included populations in four subgroups: Central coast, Georgia Strait, lower Fraser River, and west Vancouver Island. An inland group included six subgroups: Nass River, Skeena River, north Thompson River, upper and mid-Fraser River, south Thompson River, and lower Thompson River. The geographic extents of the inland and coastal groups largely coincided with the geographic distributions of stream- and ocean-type juvenile forms and may reflect postglacial colonization by two ancestral lineages that survived in Pleistocene refugia. The presence of genetically undifferentiated stream-type fish in coastal streams populated by ocean-type fish may reflect either postglacial life history differentiation from ancestral ocean-type fish or life history flexibility of ocean-type fish.
• THE SYNTHESIS OF SOME IODATED DIPHENYL-SULFIDE PHENOLS¹
  作者：Shailer L. Bass、Treat B. Johnson

  DOI：10.1021/ja01366a050

  日期：1930.3
• Wilkinson et al., Biochemical Journal, 1953, vol. 54, p. 491
  作者：Wilkinson et al.

  DOI：——

  日期：——