5-(benzo[d][1,3]dioxol-5-yl)-2H-tetrazole | 118923-32-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 5-(benzo[d][1,3]dioxol-5-yl)-2H-tetrazole
• 英文别名: 5-(1,3-benzodioxol-5-yl)-1H-tetrazole；5-(1,3-benzodioxol-5-yl)-2H-tetrazole
• CAS: 118923-32-3
• 化学式: C₈H₆N₄O₂
• mdl: MFCD02314193
• 分子量: 190.161
• InChiKey: RGZDBHMVHIGDEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  72.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(benzo[d][1,3]dioxol-5-yl)-2H-tetrazole 在 potassium carbonate 、 一水合肼 、 溶剂黄146 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 44.0h， 生成 2-[5-(1,3-benzodioxol-5-yl)-1H-tetrazol-1-yl]-N'-[(4-ethoxyphenyl)methylidene]acetohydrazide
  参考文献：
  名称：

  Synthesis, characterization and anticancer screening of some novel piperonyl–tetrazole derivatives

  摘要：

  A series of new 1,2-substituted tetrazole derivatives were synthesized and evaluated on MCF-7 (ER positive), MDA-MB-231 and ZR-75 (ER negative) breast cancer cell lines. Out of the fourteen compounds, three compounds 10,12 and 14 showed higher inhibitory effects on MCF-7 cells. Whereas, compound 8 exhibited higher inhibition in MDA-MB-231 and ZR-75 cells at 10(-5) M concentration. Total RNA was extracted and effect of compounds on different marker genes was studied. The gene expression of CD44, BRAC and BAX were significantly affected. The compounds were screened against the HepG2 cell line, to know if they are selectively targeting specific cancers and only 1-10 percent inhibition was found at 10(-5) M concentration. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.11.008
• 作为产物：
  描述：

  1-碘-3,4-亚甲基二氧基苯 在 sodium azide 、 copper(II) oxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5-(benzo[d][1,3]dioxol-5-yl)-2H-tetrazole
  参考文献：
  名称：

  Ligand-free nano copper oxide catalyzed cyanation of aryl halides and sequential one-pot synthesis of 5-substituted-1H-tetrazoles

  摘要：

  An expedient and sequential one-pot synthesis of 5-substituted-1H-tetrazoles via [2+3] cycloaddition of aryl nitriles with sodium azide is reported. The required aryl nitriles were synthesized via the nano-copper oxide promoted cyanation of aryl iodides generated in situ. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.06.107

文献信息

• Facile one-pot preparation of 5-aryltetrazoles and 3-arylisoxazoles from aryl bromides
  作者：Eiji Kobayashi、Hideo Togo

  DOI：10.1016/j.tet.2018.06.044

  日期：2018.8

  The successive treatment of aryl bromides with n-BuLi, DMF, hydroxylamine hydrochloride, and finally diphenylphosphoryl azide provided efficiently the corresponding 5-aryltetrazoles in good to moderate yields. Similarly, the successive treatment of aryl bromides with n-BuLi, DMF, hydroxylamine hydrochloride, and finally diethyl acetylenedicarboxylate and Oxone® provided efficiently the corresponding

  用正丁基锂，二甲基甲酰胺，盐酸羟胺和最后的二苯基磷酰基叠氮化物连续处理芳基溴化物，可以有效地提供相应的5-芳基四唑，并具有良好至中等的收率。类似地，与芳基溴化物的连续处理Ñ正丁基锂，DMF，盐酸羟胺，最后丁炔二酸二甲酯和过硫酸氢钾®有效地提供良好的对应的二乙基3-芳基异恶唑-4,5-二羧酸酯至适中的产率。芳族醛肟是这两个反应的关键中间体，在无过渡金属条件下，一锅中可从芳基溴化物中获得5-芳基四唑和3-芳基异恶唑。
• Diphenyl phosphate creatine immobilized on magnetite nanoparticles: an efficient and recyclable catalyst for Aza-Michael reaction
  作者：Farzane Pazoki、Fahimeh Mohammadpanah、Arefe Salamat Manesh、Jamshid Azarnia Mehraban、Akbar Heydari

  DOI：10.1007/s12039-019-1721-7

  日期：2020.12

  Abstract In this paper, diphenyl phosphate creatine was successfully immobilized on Fe3O4 nanoparticles and used as the highly efficient catalyst for the aza-Michael reaction of 5-substituted tetrazole and α,β-unsaturated carbonyl. The prepared nanocatalyst was fully analyzed by various techniques such as Fourier-transform Infrared Spectroscopy (FT-IR), Field Emission Scanning electron microscope (FE-SEM)

  摘要 本文成功地将磷酸二苯酯肌酸固定在Fe 3 O 4纳米颗粒上，并用作5-取代四唑与α，β-不饱和羰基的氮杂-迈克尔反应的高效催化剂。通过傅立叶变换红外光谱（FT-IR），场发射扫描电子显微镜（FE-SEM），振动样品磁强计（VSM），热重分析（TGA）和X射线等各种技术对制备的纳米催化剂进行了全面分析。衍射（XRD）。该方法具有许多优点，例如后处理简单，产率高和反应时间短。 图形摘要 本文讨论了一种 通过 四氢呋喃合成取代四唑的方法 Fe 3 O 4 @磷酸二苯酯肌酸纳米颗粒作为新型催化剂的aza-Michael反应。
• NOVEL TETRAZOLO HYDRAZINE DERIVATIVES AND PHARMACEUTICAL COMPOSITION COMPRISING SAME AS ACTIVE INGREDIENT FOR PREVENTING OR TREATING CANCER
  申请人：INDUSTRY-ACADEMIC COOPERATION FOUNDATION, YEUNGNAM UNIVERSITY

  公开号：US20150291566A1

  公开（公告）日：2015-10-15

  Provided are novel tetrazolo hydrazone derivatives or pharmaceutically acceptable salts thereof. The derivatives and the salts may inhibit the proliferation of cancer cells in a low molar concentration and inhibit the activity of cancer cells through the regulation of expression of apoptosis-related genes or the like, thus expressing excellent anti-cancer activity, and therefore, can be used effectively in preventing or treating cancer.

  提供的是新颖的四唑并吡啶脒衍生物或其药学上可接受的盐。这些衍生物和盐在低摩尔浓度下能抑制癌细胞的增殖，并通过调节凋亡相关基因的表达等方式抑制癌细胞活性，因此表现出优异的抗癌活性，从而能有效地用于预防或治疗癌症。
• n-Bu₄NI-catalyzed direct amination of ethers with aryl tetrazoles and triazoles via cross-dehydrogenative coupling reaction
  作者：Liang Wang、Kai-qiang Zhu、Wen-ting Wu、Qun Chen、Ming-yang He

  DOI：10.1039/c5cy00229j

  日期：——

  An efficient, metal-free protocol for direct amination of ethers with aryl tetrazoles and triazoles has been developed using the TBAI/TBHP system.

  一种高效的无金属直接醚类化合物与芳基四唑和三唑进行氨基化的方法已经开发出来，使用TBAI/TBHP体系。
• Synthesis and evaluation of the HIF-1α inhibitory activities of novel ursolic acid tetrazole derivatives
  作者：Lin-Hao Zhang、Zhi-Hong Zhang、Ming-Yue Li、Zhi-Yu Wei、Xue-Jun Jin、Hu-Ri Piao

  DOI：10.1016/j.bmcl.2019.04.028

  日期：2019.6

  metastasis. Therefore, the inhibition of this pathway is an important therapeutic target for the treatment of various types of cancers. Here, we designed and synthesized 31 ursolic acid (UA) derivatives containing a tetrazole moiety and evaluated them for their potential anti-tumor activities as HIF-1α transcriptional inhibitors. Of these, compound 14d (IC50 0.8 ± 0.2 µM) displayed the most potent activity

  缺氧诱导因子-1α（HIF-1α）通路与肿瘤血管生成，生长和转移有关。因此，抑制该途径是治疗各种类型癌症的重要治疗靶标。在这里，我们设计和合成了31个含有四唑部分的熊果酸（UA）衍生物，并对其作为HIF-1α转录抑制剂的潜在抗肿瘤活性进行了评估。其中，化合物14d（IC50 0.8±0.2 µM）表现出最强的活性，化合物14a（IC50 4.7±0.2 µM）表现出最有前途的生物学特性。对这些化合物与HIF-1α的构效关系的分析表明，位于UA衍生物C-28处的四唑基的存在对其抑制活性至关重要。