N-methyl-[14C]-formanilide | 53197-55-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-methyl-[14C]-formanilide
• 英文别名: N-methyl-N-phenylformamide
• CAS: 53197-55-0
• 化学式: C₈H₉NO
• 分子量: 137.155
• InChiKey: JIKUXBYRTXDNIY-WGGUOBTBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.28
• 重原子数：
  10.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  N-methyl-[14C]-formanilide 、 2,5-二(2-噻吩基)呋喃 在 正丁基锂 、 四甲基乙二胺 作用下， 以 乙醚 为溶剂， 生成
  参考文献：
  名称：

  Selective toxicity of the tricyclic thiophene NSC 652287 in renal carcinoma cell lines

  摘要：

  The tricyclic compound 2,5-bis(5-hydroxymethyl-2-thienyl)fura (NSC 652287) has shown a highly selective pattern of differential cytotoxic activity in the tumor cell lines comprising the National Cancer Institute (NCI) Anticancer Drug Screen. The mechanism underlying the selective cytotoxicity is unknown. We hypothesized that differential sensitivity to the compound observed in several renal tumor cell lines could be the result of selective accumulation or differential metabolism of this agent. We demonstrated here that the capacity of certain renal cell lines to accumulate and retain the compound, determined by accumulation of [(14)C]NSC 652287-derived radioactivity and by flow cytometric determination of unlabeled compound, paralleled the sensitivity of the renal cell lines re, growth inhibition by NSC 652287: A-498 > TK-10 >> ACHN similar to UO-31. The ability of the cell lines to metabolize [(14)C]NSC 652287 to a reactive species capable of binding covalently to cellular macromolecules also directly correlated with sensitivity to the compound. Different patterns of metabolites were generated by relatively more drug-sensitive cell lines in comparison with drug-resistant cell lines. The metabolizing capacity for NSC 652287 was localized primarily to the cytosolic (S100) fraction. The rate of metabolism in the cytosolic fraction from the most sensitive renal cell line, A-498, was faster than that observed in the cytosolic fractions from the other, less sensitive cell lines. The data support the hypothesis that both selective cellular accumulation and the capacity to metabolize NSC 652287 to a reactive species by certain renal carcinoma cell types are the basis fur the differential cytotoxicity of this compound class. BIOCHEM PHARMACOL 57;11:1283-1295, 1999. (C) 15)99 Elsevier Science Inc.

  DOI：

  10.1016/s0006-2952(99)00046-5
• 作为产物：
  描述：

  N-甲基苯胺 、 benzyl [14C]-formate 反应 48.0h， 以69%的产率得到N-methyl-[14C]-formanilide
  参考文献：
  名称：

  辣根过氧化物酶对 N-环丙胺的 N-脱烷基化。环丙基的命运

  摘要：

  环丙胺使催化其氧化性 N-脱烷基化的细胞色素 P450 酶失活。两个过程中的一个关键中间体被假定为通过氮中心的单电子转移 (SET) 氧化形成的高活性胺阳离子自由基，但对此的直接证据仍然难以捉摸。为了解决这一缺陷并确定 N-脱烷基化后环丙基丢失的命运，我们研究了辣根过氧化物酶（一种众所周知的 SET 酶）对 N-环丙基-N-甲基苯胺 (3) 的氧化。为了比较，类似的研究与 N-异丙基-N-甲基苯胺 (9) 和 N,N-二甲基苯胺 (8) 平行进行。在标准过氧化条件下（HRP、H(2)O(2)、空气），HRP 在 15-30 分钟内将 8 完全氧化为 N-甲基苯胺 (4) 加甲醛，而 9 氧化得更慢（< 10% 在 60 分钟内）只产生 N-异丙基苯胺 (10) 和甲醛（不形成丙酮和 4）。与 9 的结果相反，3 的氧化在 <60 分钟内完成并提供 4（20% 产率）加上痕量苯胺。通过使用

  DOI：

  10.1021/ja0111479

文献信息

• A convenient synthesis of14C-labelled resveratrol
  作者：Dongli Zeng、Qixi Mi、Hongfang Sun、Haifang Wang

  DOI：10.1002/jlcr.806

  日期：2004.3.15

  Resveratrol (trans-3,4′,5-trihydroxystilbene) is a naturally occurring phytoalexin and polyphenol existing in grapes and various plants. It shows remarkable beneficial bioactivities in the prevention of cancer, inflammation and platelet aggregation, etc. This paper reports the synthesis of [β-14C]-trans-resveratrol using 14C-formic acid (exchanged with sodium 14C-formate) and 3,5-dihydroxybenzoic acid as the starting materials. [14C-formyl]-4-methoxybenzaldehyde and diethyl 3,5-dimethoxy benzylphosphonate reacted following the Wittig–Horner reaction to give trans-3,4′,5-[β-14C]-trimethoxystilbene. The final product was obtained through the demethylation of trans-3,4′,5-[β-14C]-trimethoxystilbene and identified by TLC and UV spectroscopy. Adoption of the whole procedure provided 14C-resveratrol with a specific radioactivity of 40.8 µCi/mmol, chemical yield of 15.3% and radiochemical yield of 12.5%. Copyright © 2004 John Wiley & Sons, Ltd.

  白藜芦醇（反式-3,4',5-三羟基芪）是一种天然植物抗毒素和多酚物质，存在于葡萄和各种植物中。它在预防癌症、炎症和血小板聚集等方面显示出显著的有益生物活性。本文报道了以14C-甲酸（与14C-甲酸钠交换）和3,5-二羟基苯甲酸为原料合成[β-14C]-反式白藜芦醇的方法。[14C-甲酰基]-4-甲氧基苯甲醛和二乙基3,5-二甲氧基苄基膦酸酯通过Wittig-Horner反应得到反式-3,4'-5-[β-14C]-三甲氧基芪。最终产物通过反式-3,4'-5-[β-14C]-三甲氧基芪的脱甲基化获得，并通过TLC和UV光谱鉴定。该方法合成的14C-白藜芦醇比活性为40.8 µCi/mmol，化学产率为15.3%，放射化学产率为12.5%。版权所有 © 2004 John Wiley & Sons, Ltd.
• Synthesis of carbon-14 labeled 1-(2-hydroxyiminomethyl)-1-pyridino-3-(4-carbamoyl-1-pyridino)-2-oxapropane dichloride monohydrate ([14C]HI-6 · H2O)
  作者：M. Amin、C. E. Twine、J. A. Kepler

  DOI：10.1002/(sici)1099-1344(199711)39:11<875::aid-jlcr32>3.0.co;2-m

  日期：1997.11

  The synthesis of the title compound ([ 14 C]-2) is described. Simultaneous quaternizations of 2-pyridine[ 14 C]aldoxime (8) and isonicotinamide (10) by bis(methylsulfonoxymethyl) ether gave 1-(2-hydroxyimino-[ 14 C]methyl)-1-pyridino-3-(4-carbamoyl-1-pyridino)-2-oxapropane dimethanesulfonate (11) which was converted to [ 14 C]-2 by ion-exchange chromatography. Purification of [ 14 C]-2 was done by

  描述了标题化合物([ 14 C]-2)的合成。2-吡啶[ 14 C]醛肟 (8) 和异烟酰胺 (10) 通过双 (甲基磺氧基甲基) 醚同时季铵化得到 1-(2-羟基亚氨基-[ 14 C] 甲基)-1-吡啶基-3-(4-氨基甲酰基-1-吡啶基)-2-氧杂丙烷二甲磺酸盐(11)，通过离子交换色谱法将其转化为[ 14 C]-2。[ 14 C]-2 的纯化通过同位素稀释的连续结晶进行，其分别产生97%和98%放射化学和化学纯度的产物，总放射化学产率为3%。
• 一种放射性同位素碳-14标记瑞德西韦及其制备方法
  申请人：浙江爱索拓科技有限公司

  公开号：CN114478151B

  公开（公告）日：2024-01-12

  本申请公开一种放射性同位素碳‑14标记瑞德西韦及其制备方法，所述碳‑14标记位点为瑞德西韦分子中吡咯并[2,1‑f][1,2,4]三嗪标记单元的4‑位碳原子，其结构式如下：#imgabs0#星号标示碳‑14标记位点。
• Enzymatic <i>N</i>-Dealkylation of an <i>N</i>-Cyclopropylamine:  An Unusual Fate for the Cyclopropyl Group
  作者：Christopher L. Shaffer、Martha D. Morton、Robert P. Hanzlik

  DOI：10.1021/ja003048l

  日期：2001.1.1
• NICOLAS, C.;MADELMONT, J. C.;MAURIZIS, J. C.;GARRIGUE, H.;MEYNIEL, J. M.;+, J. LABELL. COMPOUNDS AND RADIOPHARM., 28,(1990) N2, C. 1375-1383
  作者：NICOLAS, C.、MADELMONT, J. C.、MAURIZIS, J. C.、GARRIGUE, H.、MEYNIEL, J. M.、+

  DOI：——

  日期：——