6,19-Dimethyl-3,6,9,16,19,22-hexaazatricyclo[22.2.2.2<11,14>]triaconta-1(27),11,13,24(28),25,29-hexaene | 1197155-04-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 6,19-Dimethyl-3,6,9,16,19,22-hexaazatricyclo[22.2.2.2<11,14>]triaconta-1(27),11,13,24(28),25,29-hexaene
• 英文别名: 6,19-dimethyl-3,6,9,16,19,22-hexazatricyclo[22.2.2.211,14]triaconta-1(27),11,13,24(28),25,29-hexaene
• CAS: 1197155-04-6
• 化学式: C₂₆H₄₂N₆
• 分子量: 438.66
• InChiKey: MVNLFKRBVYDYEV-UHFFFAOYSA-N

物化性质

• 熔点：
  88 °C
• 沸点：
  617.3±50.0 °C(Predicted)
• 密度：
  0.961±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  32
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  54.6
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6,19-Dimethyl-3,6,9,16,19,22-hexaazatricyclo[22.2.2.2<11,14>]triaconta-1(27),11,13,24(28),25,29-hexaene 在 氢溴酸 作用下， 以 甲醇 、 水 为溶剂， 生成
  参考文献：
  名称：

  A new hexaaminomacrocycle for ditopic binding of bromide

  摘要：

  A hexaaminomacrocycle L. containing four secondary and two tertiary amines has been synthesized and crystallized with hydrobromic acid. The structural analysis of the bromide complex Suggests that the ligand in its tetra protonated form. is involved in coordinating two bromides from both the sides via hydrogen bonding interactions with N Br distance of 3 351 angstrom, forming a ditopic complex The other two bromides are Outside the cavity, and singly bonded to the macrocycle The molecules are packed showing layer structures in which the internal bromides are locked between the layers of macrocyles The bromide anions are coordinated alternatively by one and two hydrogen bonds with the protonated amines from the two adjacent macrocycles (C) 2009 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tetlet.2009.09.041
• 作为产物：
  描述：

  在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 6,19-Dimethyl-3,6,9,16,19,22-hexaazatricyclo[22.2.2.2<11,14>]triaconta-1(27),11,13,24(28),25,29-hexaene
  参考文献：
  名称：

  新型大环双核铜 (II) 配合物的阴离子识别和传感：碘化物的选择性受体

  摘要：

  大环双核铜配合物 [Cu 2 II ( 1 )Br 3 (H 2 O)] Br 已合成并通过 X 射线晶体学表征，其中大环折叠形成碗状腔。通过紫外-可见光谱在水-乙腈 (1:3, v/v) 和水中研究了受体对卤化物的传感能力。结果表明，新受体对碘化物表现出很强的亲和力和选择性。

  DOI：

  10.1021/ic100686m

文献信息

• Synthetic Receptors Induce Anti Angiogenic and Stress Signaling on Human First Trimester Cytotrophoblast Cells
  作者：Ahmed Pantho、Mason Price、AHM Ashraf、Umaima Wajid、Maryam Khansari、Afsana Jahan、Syeda Afroze、Md Rhaman、Corey Johnson、Thomas Kuehl、Md. Hossain、Mohammad Uddin

  DOI：10.3390/ijerph14050517

  日期：——

  The cytotrophoblast (CTB) cells of the human placenta have membrane receptors that bind certain cardiotonic steroids (CTS) found in blood plasma. One of these, marinobufagenin, is a key factor in the etiology of preeclampsia. Herein, we used synthetic receptors (SR) to study their effectiveness on the angiogenic profile of human first trimester CTB cells. The humanextravillous CTB cells (Sw.71) used in this study were derived from first trimester chorionic villus tissue. Culture media of CTB cells treated with ≥1 nM SR level revealed sFlt-1 (Soluble fms-like tyrosine kinase-1) was significantly increased while VEGF (vascular endothelial growth factor) was significantly decreased in the culture media (* p < 0.05 for each) The AT2 receptor (Angiotensin II receptor type 2) expression was significantly upregulated in ≥1 nM SR-treated CTB cells as compared to basal; however, the AT1 (Angiotensin II receptor, type 1) and VEGFR-1 (vascular endothelial growth factor receptor 1) receptor expression was significantly downregulated (* p < 0.05 for each). Our results show that the anti-proliferative and anti-angiogenic effects of SR on CTB cells are similar to the effects of CTS. The observed anti angiogenic activity of SR on CTB cells demonstrates that the functionalized-urea/thiourea molecules may be useful as potent inhibitors to prevent CTS-induced impairment of CTB cells.

  人类胎盘的细胞滋养层细胞（CTB）具有膜受体，这些受体能结合血浆中发现的某些强心类固醇（CTS）。其中一种称为金线蛙甾醇，是子痫前期发病机制中的关键因素。本文中，我们利用合成受体（SR）来研究它们对人类孕早期CTB细胞的血管生成特征的有效性。本研究所用的外滋养层人类CTB细胞（Sw.71）源自孕早期的绒毛组织。经≥1 nM SR水平处理的CTB细胞培养基显示出可溶性酪氨酸激酶受体Fms样1（sFlt-1）显著增加，而血管内皮生长因子（VEGF）显著减少（* p < 0.05）。与基础水平相比，≥1 nM SR处理的CTB细胞中，血管紧张素II受体2型（AT2）表达显著上调；而血管紧张素II受体1型（AT1）和血管内皮生长因子受体1（VEGFR-1）的表达则显著下调（* p < 0.05）。我们的结果表明，SR对CTB细胞的抗增殖和抗血管生成作用与CTS的作用相似。SR在CTB细胞上展现的抗血管生成活性表明，功能化的脲/硫脲分子可能作为强效抑制剂，用以预防CTS诱导的CTB细胞功能障碍。
• Colourimetric and fluorescent detection of oxalate in water by a new macrocycle-based dinuclear nickel complex: a remarkable red shift of the fluorescence band
  作者：Md Mhahabubur Rhaman、Frank R. Fronczek、Douglas R. Powell、Md. Alamgir Hossain

  DOI：10.1039/c3dt53467g

  日期：——

  A new macrocycle-based dinuclear nickel chemosensor selectively binds oxalate anions both in solution and the solid state, displaying a remarkable red shift of the fluorescence band with a visible colour change in water at physiological pH in the presence of an external dye.

  一种新的基于大环的双核镍化学传感器选择性地结合溶液和固态中的草酸根阴离子，在存在外部染料的情况下，在生理 pH 值的水中显示出显着的荧光带红移和可见的颜色变化。
• Encapsulation and selective recognition of sulfate anion in an azamacrocycle in water
  作者：John S. Mendy、Marcy L. Pilate、Toyketa Horne、Victor W. Day、Md. Alamgir Hossain

  DOI：10.1039/c0cc01699c

  日期：——

  Structural characterization of a sulfate complex with an azamacrocycle suggests that one sulfate is encapsulated in the macrocyclic cavity with eight hydrogen bonds; a significant selectivity of the host was observed for sulfate over halides, nitrate and perchlorate as evaluated by 1H NMR studies in water.

  一种含有氮杂大环的硫酸盐复合物的结构特征表明，一个硫酸盐被封装在大环腔内，形成了八个氢键；通过在水中的1H NMR研究评估，发现宿主对硫酸盐相对于卤化物、硝酸盐和高氯酸盐具有显著的选择性。
• Charge-Assisted Encapsulation of Two Chlorides by a Hexaprotonated Azamacrocycle
  作者：Md. Alamgir Hossain、Musabbir A. Saeed、Frank R. Fronczek、Bryan M. Wong、Kalpana R. Dey、John S. Mendy、Don Gibson

  DOI：10.1021/cg100110f

  日期：2010.4.7

  A chloride complex of a hexaprotonated azamacrocycle has been isolated, and its structure has been determined by X-ray crystallography showing two encapsulated chloride anions in the cavity. The two internal guests are coordinated at two binding sites on the opposite side of the macrocycle through trigonal recognition by hydrogen-bonding interactions. The other four chlorides are located outside the cavity, each with a single hydrogen bond from secondary amines. Ab initio calculations based on density functional theory (DFT) suggest that the encapsulation of two chlorides inside the cavity leads to a significant charge transfer from the anions to the protonated amines.
• Rational design of a macrocycle-based chemosensor for anions
  作者：Kalpana R. Dey、Bryan M. Wong、Md. Alamgir Hossain

  DOI：10.1016/j.tetlet.2010.01.004

  日期：2010.3

  A macrocycle-based fluorescence chemosensor has been designed and synthesized from the reaction of dansyl chloride and a hexaaminomacrocycle containing four secondary and two tertiary amines. The new chemosensor has been examined For its binding ability towards phosphate, sulfate, nitrate, iodide, bromide, chloride, and fluoride by fluorescence spectroscopy in DMSO. The results indicate that the compound binds each of the anions with a 11 stoichiometry, showing high affinity for oxoanions, chloride, and iodide with binding constants up to four orders of magnitude Ab initio calculations based on density functional theory (DFT) suggest that the ligand is deformed in order to encapsulate in anion, and each anion, except fluoride, is bonded to the macrocycle through two NH X- and four CH X- interactions (C) 2010 Elsevier Ltd All rights reserved.