N-hydroxyethyl exo-7-oxabicyclo[2.2.1]heptane-2,3-dicarboximide | 245092-42-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-hydroxyethyl exo-7-oxabicyclo[2.2.1]heptane-2,3-dicarboximide
• 英文别名: 4-(2-hydroxyethyl)-10-oxa-4-azatricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione；(3aR,4S,7R,7aS)-2-(2-hydroxyethyl)-3a,4,5,6,7,7a-hexahydro-1H-4,7-epoxyisoindole-1,3(2H)-dione；exo-cis-7-Oxa-bicyclo<2.2.1>heptan-dicarbonsaeure-(2,3)-<2-hydroxy-ethylimid>；4-aza-4-(2-hydroxyethyl)-10-oxatricyclo[5.2.1.0]decane-3,5-dione；2-(2-hydroxy-ethyl)-(3at,7at)-hexahydro-4r,7c-epioxido-isoindole-1,3-dione；4-(2-hydroxyethyl)-4-aza-10-oxatricyclo[5.2.1.0(2,6)]decane-3,5-dione；(3aS,4R,7S,7aR)-2-(2-hydroxyethyl)-3a,4,5,6,7,7a-hexahydro-4,7-epoxyisoindole-1,3-dione
• CAS: 245092-42-6
• 化学式: C₁₀H₁₃NO₄
• 分子量: 211.218
• InChiKey: QQXHRXWQSQDDDA-KVFPUHGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-hydroxyethyl exo-7-oxabicyclo[2.2.1]heptane-2,3-dicarboximide 在 三乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 6.0h， 生成 2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethyl 2-bromo-2-methylpropanoate
  参考文献：
  名称：

  Design and Synthesis of N-Maleimido-Functionalized Hydrophilic Polymers via Copper-Mediated Living Radical Polymerization:  A Suitable Alternative to PEGylation Chemistry

  摘要：

  A series of a-functional maleimide polymethacrylates (M-n = 4.1-35.4 kDa, PDi = 1.06-1.27) have been prepared via copper-catalyzed living radical polymerization (LRP). Two independent synthetic protocols have been successfully developed and the polymers obtained in multigram scale, with an 80-100% content of maleimide reactive chain ends, depending on the method employed. A method for the synthesis of amino-terminated polymers, starting from Boc-protected amino initiators, has also been developed, as these derivatives are key intermediates in one of the two processes studied in the present work. The alternative synthetic pathway involves an initiator containing a maleimide unit "protected" as a Diels-Alder adduct. After the polymerization step, the maleimide functionality has been reintroduced by retro-Diels -Alder reaction, by simply refluxing those polymers in toluene for 7 h. These maleimido-terminated materials, poly(methoxyPEG((475))) methacrylates and poly(glycerol) methacrylates, differ for both the nature and size of the polymer side branches and showed an excellent solubility in water, a property that made them an ideal candidate for the synthesis of new polymer- (poly) peptide biomaterials. These functional polymers have been successfully employed in conjugation reactions in the presence of thiol-containing model substrates, namely, reduced glutathione (gamma-Glu-Cys-Gly) and the carrier protein, bovine serum albumin (BSA), in 100 mM phosphate buffer (pH 6.8-7.4) and ambient temperature.

  DOI：

  10.1021/ja0430999
• 作为产物：
  描述：

  exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride 在 palladium 10% on activated carbon 、 氢气 、 三乙胺 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 18.0h， 生成 N-hydroxyethyl exo-7-oxabicyclo[2.2.1]heptane-2,3-dicarboximide
  参考文献：
  名称：

  具有末端磷酸酯的降冰片胺类似物及其抗癌活性

  摘要：

  将具有末端醇（乙醇，丙醇，丁醇，戊醇，己醇和环己醇）部分的降冰素烷类似物家族用氯二乙基，氯二苯基或氯双-三-三氯乙基磷酸处理，以提供高度集中的相应磷酸酯的文库。随后针对九种人类癌细胞系进行的生物学筛选确定了磷酸酯掩盖的难易程度（磷酸酯水解）和细胞死亡之间的趋势。最有效的类似物具有联苯或双三氯乙基部分。还用通常更有效的己基类似物检查了烷基间隔基的作用。4-氮杂-4-（3- {双（2,2,2-三氯乙基）磷酸盐}丙基）-10-氧三环[5.2.1.0]癸烷-3,5-二酮（10b）是最有效的类似物，在一组9种人类癌细胞系中合成的平均GI 50为11μM：结肠癌（HT29和SW480）; 乳腺癌（MCF-7）；卵巢癌（A2780）；肺癌（H460）; 皮肤癌（A431）; 前列腺癌（DU145）; 神经元癌（BE2-C）和脑癌（SJ-G2）。相对于铅，降冰片素，抗增殖活性提高了五倍。

  DOI：

  10.1016/j.bmc.2011.01.031

文献信息

• Norcantharimides, synthesis and anticancer activity: Synthesis of new norcantharidin analogues and their anticancer evaluation
  作者：Timothy A. Hill、Scott G. Stewart、Stephen P. Ackland、Jayne Gilbert、Benjamin Sauer、Jennette A. Sakoff、Adam McCluskey

  DOI：10.1016/j.bmc.2007.06.034

  日期：2007.9

  A range of amines was reacted with norcantharidin (2) to provide the corresponding norcantharimides (9-43). Treatment of norcantharidin with allylamine afforded the corresponding allyl-norcantharimide (20) which was amenable to epoxidation (mCPBA, 22) and subsequent ring opening (MeOH/H(+); 23) or alternatively, osmylation (OsO(4)/NMO; 24). These simple synthetic modifications of 2 facilitated the

  使一定范围的胺与降冰毒烷素（2）反应以提供相应的降冰毒胺（9-43）。用烯丙胺处理降冰草烷素得到相应的烯丙基-去甲癸酰胺（20），其适合于环氧化（mCPBA，22）和随后的开环（MeOH / H（+）； 23）或可进行的osmylation（OsO（4）/ NMO； N / O）。 24）。这些对2的简单合成修饰促进了一系列新的降冰片内酰胺类化合物的开发，它们显示出对HT29和SW480（结直肠癌）的中等至良好的广谱细胞毒性。MCF-7（乳腺腺癌）；A2780（卵巢癌）; H460（肺癌）；A431（表皮样癌）；DU145（前列腺癌）; BE2-C（神经母细胞瘤）；和SJ-G2（胶质母细胞瘤）。具有C（10）的类比，
• Norcantharidin analogues with nematocidal activity in Haemonchus contortus
  作者：Bronwyn E. Campbell、Mark Tarleton、Christopher P. Gordon、Jennette A. Sakoff、Jayne Gilbert、Adam McCluskey、Robin B. Gasser

  DOI：10.1016/j.bmcl.2011.04.031

  日期：2011.6

  anthelmintic drugs, there is an urgent need to develop new nematocides. In the present study, we employed a targeted approach for the design of a series of norcantharidin analogues (n = 54) for activity testing against the barber’s pole worm (Haemonchus contortus) of small ruminants in a larval development assay (LDA) and also for toxicity testing on nine distinct human cell lines. Although none of the

  由于家畜的寄生线虫对驱虫药具有抗性的主要问题，迫切需要开发新的杀线虫剂。在本研究中，我们采用有针对性的方法设计了一系列norcantharidin类似物（n  = 54），用于在幼虫发育测定法（LDA）中针对小反刍动物的理发店极杆蠕虫（Haemonchus contortus）进行活性测试，以及对九种不同的人类细胞系进行毒性测试。尽管合成的54个类似物均对这些细胞系均无毒性，但其中三个（N-辛基-7-氧杂双环（2.2.1）庚烷-2,3-二甲酰亚胺（B2），N-癸基-7-氧杂双环（2.2.1）庚烷-2,3-二甲酰亚胺（B3）和4-[（4-甲基）-3-乙基-2-甲基-5-苯基呋喃-10-氧杂-4-氮杂三环[5.2.1]癸烷-3,5-二酮（B21）可重复显示99-100 LD 50中25 ％至40μM的LDA对捻转血杆菌的致死率％。高“命中率”（5.6％）表明，此处采用的方法比常规药物筛选方法具
• Structural and theoretical study of four novel norcantharidine derivatives: two new cases of conditional isomorphism
  作者：Xue-Jie Tan、Shuai Liu、Xiao-Ming Hei、Feng-Cun Yang、Peng-Bing He、Feng Guo、Dian-Xiang Xing

  DOI：10.1107/s2053229619016164

  日期：2020.1.1

  packing types cannot be ruled out. On the other hand, isomorphism may just be the result of kinetic possibilities instead of relative thermodynamic stabilities. Though crystal structure prediction is formidable, the comparison method based on existing crystal structures and quantum calculations can be used to predict the probability of isomorphism. This understanding will help us to design new norbornene

  四种新颖的5,6-脱氢降冰片烷（DNCA）/降冰片烷（NCA）衍生物，即（3aR，4S，7R，7aS）-2-苯基-3a，4,7,7a-四氢-4,7的结构和理论研究-环氧-1H-异吲哚-1,3（2H）-二酮，C14H11NO3（DNCA-A），（3aR，4S，7R，7aS）-2-（4-硝基苯基）-3a，4,7,7a-四氢-4,7-环氧-1H-异吲哚-1,3（2H）-二酮，C14H10N2O5（DNCA-NA），（3aR，4S，7R，7aS）-2-（4-硝基苯基）-3a，4,5 ，6,7,7a-六氢-1H-4,7-环氧异吲哚-1,3（2H）-二酮，C14H12N2O5（NCA-NA）和（3aR，4S，7R，7aS）-2-（2-羟乙基报道了-3a，4,5,6,7,7a-六氢-1H-4,7-环氧异吲哚-1,3（2H）-二酮，C10H13NO4（NCA-AE）。这些分子的超分子相互作用和单晶结构特征
• Bicyclic Imides and Isoindolines¹
  作者：Charles H. Grogan、Leonard M. Rice

  DOI：10.1021/jm00342a042

  日期：1963.11
• Synthesis of Glycerophospholipid Conjugates of Cantharidin and Its Analogues
  作者：Zheng-Hong Zhou、Ru-Yu Chen

  DOI：10.1080/00397910008087266

  日期：2000.10

  A series of glycerophospholipid conjugates of cantharidin and its analogues were synthesized in a one-pot reaction, using hexaehtyl phosphorus triamide, activated by a catalytic amount of iodine, as the phosphorylating reagent. The structures of the title compounds were confirmed by H-1 NMR, P-31 NMR, IR and elemental analysis.