4-(2-piperonylamino-ethyl)-phenol | 500731-43-1

• 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: 4-(2-piperonylamino-ethyl)-phenol
• 英文别名: 4-(2-Piperonylamino-aethyl)-phenol；N-(3,4-Methylendioxybenzyl)-4-hydroxyphenethylamin；4-[2-(1,3-Benzodioxol-5-ylmethylamino)ethyl]phenol
• CAS: 500731-43-1
• 化学式: C₁₆H₁₇NO₃
• 分子量: 271.316
• InChiKey: MXFRBNZPZXWCAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  50.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(2-piperonylamino-ethyl)-phenol 在 2,2,2-三氟乙醇 、 [双(三氟乙酰氧基)碘]苯 作用下， 反应 48.5h， 生成 6'-oxospiro[7,8-dihydro-5H-[1,3]dioxolo[4,5-h][2]benzazepine-9,3'-cyclohexa-1,4-diene]-6-carbaldehyde
  参考文献：
  名称：

  Synthesis of Amaryllidaceae alkaloids, siculine, oxocrinine, epicrinine, and buflavine

  摘要：

  Three crinane type of alkaloids isolated from Amaryllidaceae family were synthesized by taking advantage of the PIFA-mediated intramolecular p-p' diphenol coupling reaction of norbelladine derivatives. Furthermore, buflavine was also prepared by using the p-p' diphenol coupling followed by dienone-phenol rearrangement as a key step. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.03.087
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 sodium amalgam 、 乙醇 作用下， 生成 4-(2-piperonylamino-ethyl)-phenol
  参考文献：
  名称：

  DE259193

  摘要：

  公开号：

文献信息

• 5,10b-Ethanophenanthridine amaryllidaceae alkaloids inspire the discovery of novel bicyclic ring systems with activity against drug resistant cancer cells
  作者：Sean Henry、Ria Kidner、Mary R. Reisenauer、Igor V. Magedov、Robert Kiss、Véronique Mathieu、Florence Lefranc、Ramesh Dasari、Antonio Evidente、Xiaojie Yu、Xiuye Ma、Alexander Pertsemlidis、Regina Cencic、Jerry Pelletier、David A. Cavazos、Andrew J. Brenner、Alexander V. Aksenov、Snezna Rogelj、Alexander Kornienko、Liliya V. Frolova

  DOI：10.1016/j.ejmech.2016.05.004

  日期：2016.9

  alkaloids and non-basic secondary metabolites, many of which are investigated for their promising anticancer activities. Of these, crinine-type alkaloids based on the 5,10b-ethanophenanthridine ring system were recently shown to be effective at inhibiting proliferation of cancer cells resistant to various pro-apoptotic stimuli and representing tumors with dismal prognoses refractory to current chemotherapy

  石蒜科的植物产生各种各样的生物碱和非碱性次生代谢产物，其中许多因其有希望的抗癌活性而被研究。其中，最近显示基于5,10b-乙基菲啶环系统的可丽宁型生物碱可有效抑制对各种促凋亡刺激具有抵抗力的癌细胞的增殖，并代表对当前化疗难以耐受的肿瘤，例如神经胶质瘤，黑色素瘤，非小细胞肺癌，食道癌，头颈癌等。以这一发现为出发点，并利用简洁的仿生路线通往可丽宁骨架，合成了一系列可丽宁类似物，并针对癌细胞进行了评估。这些化合物表现出一位数的微摩尔活性，并在多种耐药性癌细胞培养物中保留了这种活性。这项研究导致发现了新的双环系统，在开发能够克服癌症化疗耐药性的有效临床抗癌药物中具有巨大潜力。
• METHODS FOR TREATMENT OF RESISTANT CANCER
  申请人：New Mexico Tech Research Foundation

  公开号：US20170313720A1

  公开（公告）日：2017-11-02

  The present disclosure describes a method to treat conditions, including cancer, using compounds that can target resistant cancer cells. The compounds of the invention can decrease the rate of proliferation of drug-resistant cancer cells, such as glioma, lung cancer, and uterine sarcoma.

  本公开描述了一种治疗条件（包括癌症）的方法，使用可以靶向耐药癌细胞的化合物。本发明的化合物可以降低药物耐药癌细胞（如胶质瘤、肺癌和子宫肉瘤）的增殖速率。
• Methods for treatment of resistant cancer
  申请人：New Mexico Tech University Research Park Corporation

  公开号：US10414778B2

  公开（公告）日：2019-09-17

  The present disclosure describes a method to treat conditions, including cancer, using compounds that can target resistant cancer cells. The compounds of the invention can decrease the rate of proliferation of drug-resistant cancer cells, such as glioma, lung cancer, and uterine sarcoma.

  本公开内容描述了一种利用可靶向抗药性癌细胞的化合物治疗包括癌症在内的各种疾病的方法。本发明的化合物可以降低抗药性癌细胞的增殖速度，如胶质瘤、肺癌和子宫肉瘤。
• DE259874
  申请人：——

  公开号：——

  公开（公告）日：——
• [EN] METHODS FOR TREATMENT OF RESISTANT CANCER<br/>[FR] MÉTHODES POUR LE TRAITEMENT D'UN CANCER RÉSISTANT
  申请人：NEW MEXICO TECH RES FOUND

  公开号：WO2017189834A1

  公开（公告）日：2017-11-02

  The present disclosure describes a method to treat conditions, including cancer, using compounds that can target resistant cancer cells. The compounds of the invention can decrease the rate of proliferation of drug-resistant cancer cells, such as glioma, lung cancer, and uterine sarcoma.