trans-1-(6-chrysenyl)-3-acetoxy-4-phenylazetidin-2-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: trans-1-(6-chrysenyl)-3-acetoxy-4-phenylazetidin-2-one
• 英文别名: trans-N-(6-chrysenyl)-3-acetoxy-4-phenylazetidin-2-one；[(3R,4R)-1-chrysen-6-yl-2-oxo-4-phenylazetidin-3-yl] acetate
• 化学式: C₂₉H₂₁NO₃
• 分子量: 431.491
• InChiKey: ODHJRSPLOFJCKF-VSGBNLITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  在 bismuth (III) nitrate pentahydrate 、 三乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 trans-1-(6-chrysenyl)-3-acetoxy-4-phenylazetidin-2-one
  参考文献：
  名称：

  Banik, Indrani; Yadav, Ram Naresh; Becker, Fredrick F., Journal of the Indian Chemical Society, 2018, vol. 95, # 11, p. 1373 - 1376

  摘要：

  DOI：

文献信息

• Stereocontrolled synthesis of anticancer β-lactams via the Staudinger reaction
  作者：Bimal K. Banik、Indrani Banik、Frederick F. Becker

  DOI：10.1016/j.bmc.2005.03.044

  日期：2005.6

  Stereocontrolled synthesis of novel beta-lactams using polyaromatic imines following the Staudinger reaction has been accomplished. The effects of domestic microwave irradiation on this type of reaction have been investigated. Formation of trans-beta-lactams has been explained through isomerization of the enolates formed during the reaction of acid chloride (equivalent) with imines in the presence

  在施陶丁格反应之后，已经完成了使用聚芳族亚胺的立体控制合成新的β-内酰胺的方法。已经研究了家用微波辐射对这种类型的反应的影响。通过在三乙胺存在下酰氯（当量）与亚胺反应期间形成的烯醇化物的异构化，可以解释反式β-内酰胺的形成。据信供体-受体复合物途径与顺-β-内酰胺的形成有关。已经发现，在控制所得β-内酰胺的立体化学中，氢的作用显着。SAR已鉴定出具有抗癌活性的β-内酰胺。乙酰氧基的存在已被证明对于其抗癌活性是必不可少的。
• Unprecedented stereoselectivity in the Staudinger reaction with polycyclic aromatic imines
  作者：Bimal K Banik、Frederick F Becker

  DOI：10.1016/s0040-4039(00)01126-6

  日期：2000.8

  Cycloaddition of imines derived from polycyclic aromatic amines with acid chloride (or equivalent) in the presence of triethylamine at −78°C to room temperature unexpectedly produced trans-β-lactams.

  在三乙胺的存在下，于-78°C到室温，将衍生自多环芳族胺的亚胺与酰氯（或等价物）进行环加成反应，出乎意料地产生了反式-β-内酰胺。
• Stereoselective Synthesis of β-Lactams with Polyaromatic Imines:  Entry to New and Novel Anticancer Agents
  作者：Indrani Banik、Frederick F. Becker、Bimal K. Banik

  DOI：10.1021/jm0255825

  日期：2003.1.1

  We present herein stereoselective synthesis of novel beta-lactams using polyaromatic imines following the Staudinger reaction. Consistent mechanisms for these results have been advanced. As a measure of cytotoxicity, some of these compounds have been assayed against nine human cancer cell lines. Structure-activity study has revealed that 1-N-chrysenyl and 1-N-phenanthrenyl 3-acetoxy-4-aryl-2-azetidinones

  我们在本文中提出了在Staudinger反应后使用聚芳族亚胺的新型β-内酰胺的立体选择性合成。这些结果的一致机制已得到改进。作为细胞毒性的一种测定方法，其中一些化合物已针对9种人类癌细胞系进行了分析。结构活性研究表明，1-N-芴基和1-N-菲基3-乙酰氧基-4-芳基-2-氮杂环丁烷酮具有有效的抗癌活性。β-内酰胺的C（3）处乙酰氧基的存在已被证明对于其抗癌活性是必不可少的。
• An Efficient Synthesis of Optically Active trans-(3R,4R)-3-Acetoxy-4-aryl-1-(chrysen-6-yl)azetidin-2-ones Using (+)-Car-3-ene as a Chiral Auxiliary
  作者：Aarif L. Shaikh、Orlando Esparza、Bimal K. Banik

  DOI：10.1002/hlca.201100225

  日期：2011.12

  An efficient enantioselective synthesis of 3‐acetoxy trans‐β‐lactams 7a and 7b via [2+2] cycloaddition reactions of imines 4a and 4b, derived from a polycyclic aromatic amine and bicyclic chiral acid obtained from (+)‐car‐3‐ene, is described. The cycloaddition was found to be highly enantioselective, producing only trans‐(3R,4R)‐N‐azetidin‐2‐one in very good yields. This is the first report of the

  的有效对映选择性合成的3-乙酰氧基反式- β内酰胺7A和7B 通过[2 + 2]亚胺的环加成反应图4a和4b中，从得到的多环芳族胺和双环的手性酸衍生的（+） -车-3-烯，描述。发现环加成是高度对映选择性的，仅以非常好的收率产生反式（3 R，4 R）-N-氮杂环丁烷-2-一。这是对映体纯合成的第一份报告中反式- β内酰胺7A和7B 在氮杂环丁烷环的N（1）处具有多环芳族取代基。
• Synthesis of anticancer β-lactams: mechanism of action
  作者：Bimal K. Banik、Frederick F. Becker、Indrani Banik

  DOI：10.1016/j.bmc.2004.03.033

  日期：2004.5

  Synthesis of the trans 1-N-chrysenyl and 1-N-phenanthrenyl 3-acetoxy-4-phenyl-2-azetidinones has been achieved. Microwave-assisted reaction has proved useful in the synthesis of these compounds. Cell growth inhibition study has indicated selective anticancer activity against two leukemia and colon carcinoma cell lines. A mechanistic correlation of their anticancer activity has been described. Striking G(2) blockade that is clearly distinct in cell cycle analysis and demonstrated only in sensitive cell lines has been observed. They, do not induce apoptosis in sensitive or resistant lines. They also do not inhibit topoisomerases. Ames test has shown they are nonmutagenic. (C) 2004 Published by Elsevier Ltd.