(5-碘-2,4-二氧代-3,4-二氢-2H-嘧啶-1-基)-乙酸 | 57846-83-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: (5-碘-2,4-二氧代-3,4-二氢-2H-嘧啶-1-基)-乙酸
• 英文名称: 1-carboxymethyl-5-iodouracil
• 英文别名: (5-iodouracil-1-yl)acetic acid；(5-Iodo-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetic acid；2-(5-iodo-2,4-dioxopyrimidin-1-yl)acetic acid
• CAS: 57846-83-0
• 化学式: C₆H₅IN₂O₄
• 分子量: 296.021
• InChiKey: MDDICWDYBXXXBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  86.7
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2933599090

反应信息

• 作为反应物：
  描述：

  (5-碘-2,4-二氧代-3,4-二氢-2H-嘧啶-1-基)-乙酸 在 四(三苯基膦)钯 copper(l) iodide 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 ethyl 2-[[2-[5-(3-hydroxyprop-1-ynyl)-2,4-dioxopyrimidin-1-yl]acetyl]-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]amino]acetate
  参考文献：
  名称：

  The use of Sonogashira coupling for the synthesis of modified uracil peptide nucleic acid

  摘要：

  Palladium-catalyzed Sonogashira coupling has been shown to be compatible with PNA monomers as illustrated by the reaction of 5-iodouracil peptide nucleic acid monomer (U-1-PNA) with several terminal alkynes. These reactions hake been performed in the solution Phase and with U-1-PNA linked to an insoluble polymer Support. The results presented herein shock that while the isolated yields from the solution phase chemistry are modest (38 53%), the yields of the resin-bound Coupling reactions are essentially quantitative. at the monomer level. A selection of alkynes LIS used to install various additional functionality on the uracil nucleobase, Examples of a hydroxyl, protected thiol and protected amino group are given. Further, an example of derivatization of a resin-bound oligomer with a single U-1 insert is given. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00024-2
• 作为产物：
  描述：

  tert-butyl (5-iodouracil-1-yl)acetate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 (5-碘-2,4-二氧代-3,4-二氢-2H-嘧啶-1-基)-乙酸
  参考文献：
  名称：

  Synthesis of New, Base-Modified PNA Monomers

  摘要：

  A number of N-Boc-protected peptide nucleic acids (PNA) monomers containing 5-aryl- and 5-alkynyl-uracil bases have been synthesized using different palladium-catalyzed cross-coupling reactions. Starting from the base-unprotected 5-iodo-uracil PNA monomer, only the Stille couplings were accomplished successfully, while Suzuki couplings with boronic acids containing the same aryl groups failed. During Sonogashira couplings with terminal alkynes, significant amounts of unrequired furano[2,3-d]pyrimidine by-products were formed. Protection of the lactam function by p-methoxybenzylation prevented the opportunity for intramolecular cyclization as well as formation of a negative charge on the 4-O atom, making it possible to reach almost quantitative yields at Sonogashira couplings and acceptable conversions in Suzuki reactions.

  DOI：

  10.1080/15257770701490613

文献信息

• Synthesis and antitumor activity of novel substituted uracil-1′(N)-acetic acid ester derivatives of 20(S)-camptothecins
  作者：Di-Zao Li、Qiang-Zhe Zhang、Cun-Ying Wang、Yan-Ling Zhang、Xing-Yu Li、Ji-Tao Huang、Hong-Yan Liu、Zhao-Di Fu、Hua-Xian Song、Jin-Ping Lin、Teng-Fei Ji、Xian-Dao Pan

  DOI：10.1016/j.ejmech.2016.11.013

  日期：2017.1

  selected to be evaluated for in vivo antitumor activity against H22, BGC-823 and Bel-7402 in mice. In vivo testing results indicated that 12 and 13 had antitumor activity against mouse liver carcinoma H22 close to Paclitaxel and cyclophosphamide. 12 had similar antitumor activity against human gastric carcinoma BGC-823 in nude mice compared to irinotecan (3) and possessed better antitumor activity against

  一系列新颖的取代的尿嘧啶-1'（Ñ） -乙酸的酯（6 - 20）的喜树碱（彩色显像管）的酰化方法合成。评估了这些新化合物对肿瘤细胞系A549，Bel7402，BGC-823，HCT-8和A2780的体外抗肿瘤活性。体外结果显示，与CPT（1）和拓扑替康（TPT，2）相比，大多数衍生物表现出可比或更高的细胞毒性，其中12和13具有最佳疗效。四种化合物，9，12，13和16选择用于评估小鼠中针对H 22，BGC-823和Bel-7402的体内抗肿瘤活性。体内测试结果表明，12和13具有对小鼠肝癌H 22的抗肿瘤活性，接近紫杉醇和环磷酰胺。12相比伊立替康（具有针对人胃癌BGC-823相似的抗肿瘤活性在裸鼠3）并拥有在裸鼠中对人肝癌的Bel-7402更好的抗肿瘤活性比2。还发现12显示出类似的机制，但与2相比，对拓扑异构酶I（Topo I）的抑制活性更好。这些发现表明，CPTs的20（S）-O-
• Pyrene chromophores for the photoreversal of psoralen interstrand crosslinks
  作者：Jens M. Stadler、Thorsten Stafforst

  DOI：10.1039/c4ob00603h

  日期：——

  Applying psoralen interstrand crosslinks for the photoactivation of nucleic acids is a new concept. To find chromophores that can efficiently stimulate crosslink repair we screened several pyrenes and appended them to peptide nucleic acids for their site-selective addressing. Even though pyrenes conjugated to uracil revealed desirable spectroscopic properties they were not effective in crosslink reversal. In contrast, bare pyrenes are well suitable for crosslink repair with 350 nm light showing an uncaging efficiency similar to classical photocaging groups.

  应用补骨脂素交联进行核酸的光活化是一个新概念。为了找到能有效刺激交联修复的色素，我们筛选了几种芘，并将它们附加到肽核酸上实现其位点的选择性寻址。尽管与尿嘧啶结合的芘显示出令人满意的谱学特性，但它们在交联逆转中的效果不佳。相反，未经修饰的芘相当适合进行交联修复，利用350纳米的光表现出与经典光笼组相似的去笼效率。
• NANOPORE BASED SEQUENCER
  申请人：ARIZONA BOARD OF REGENTS on behalf of ARIZONA STATE UNIVERSITY

  公开号：US20170204066A1

  公开（公告）日：2017-07-20

  The present invention is directed to systems, devices and methods for identifying biopolymers, such as strands of DNA, as they pass through a constriction such as a carbon nanotube nanopore. More particularly, the invention is directed to such systems, devices and methods in which a newly translocated portion of the biopolymer forms a temporary electrical circuit between the nanotube nanopore and a second electrode, which may also be a nanotube. Further, the invention is directed to such systems, devices and methods in which the constriction is provided with a functionalized unit which, together with a newly translocated portion of the biopolymer, forms a temporary electrical circuit that can be used to characterize that portion of the biopolymer.

  本发明涉及用于识别生物聚合物（例如DNA链）的系统、设备和方法，当它们通过像碳纳米管纳孔这样的狭窄通道时。更具体地说，本发明涉及这种系统、设备和方法，其中生物聚合物的新穿过部分在纳米管纳孔和第二电极之间形成临时电路，第二电极也可能是一个纳米管。此外，本发明涉及这种系统、设备和方法，其中通道配备有一个功能化单元，该单元与生物聚合物的新穿过部分一起形成临时电路，可用于表征生物聚合物的部分。
• Preparation and biological effects of N-tris(hydroxymethyl)methylaminocarbonylmethyl derivatives of heterocyclic bases
  作者：Helmut Pischel、Antonín Holý、Jiří Veselý、Günther Wagner

  DOI：10.1135/cccc19842541

  日期：——

  The title compounds were synthetized by the reaction of TRIS with p-nitrophenyl or alkyl esters of N-carboxymethyl derivatives of uracil, 5-chloro-, 5-bromo-, 5-iodouracil, thymine, cytosine, 6-azauracil, 2-pyridone, 2-pyrimidone, 3-pyridazone and orotic acid. The following novel N-carboxymethyl derivatives are also described: 6-azauracil derivative VIIa by condensation of 4-thio-6-azauracil with methyl bromoacetate followed by hydrolysis, 5-chloruracil derivative IIIa by chlorination of uracil compound IIa, 2-pyrimidone (IXa) and 3-pyridazone derivative Xa by the reaction of the sodium salts of the bases with sodium chloracetate. Of all the amides tested, only the 3-pyridazone derivative Xd and orotic acid derivative XIId inhibited the growth of L-1210 mouse leukemic cells in vitro with 1D₅₀ approx. 10^-4 mol l^-1.

  这个标题化合物是通过TRIS与N-羧甲基尿嘧啶衍生物、5-氯、5-溴、5-碘尿嘧啶、胸腺嘧啶、胞嘧啶、6-氮杂尿嘧啶、2-吡啶酮、2-嘧啶酮、3-吡啶唑和乳酸反应合成的。此外，还描述了以下新的N-羧甲基衍生物：通过4-硫代-6-氮杂尿嘧啶与溴乙酸甲酯缩合后水解得到的6-氮杂尿嘧啶衍生物VIIa，通过氯化尿嘧啶化合物IIa得到的5-氯尿嘧啶衍生物IIIa，以及通过碱基的钠盐与氯乙酸钠反应得到的2-嘧啶酮（IXa）和3-吡啶唑衍生物（Xa）。在测试的所有酰胺中，只有3-吡啶唑衍生物Xd和乳酸衍生物XII d能够在体外抑制L-1210小鼠白血病细胞的生长，1D50约为10-4mol/L。
• A Convenient and Scalable Synthesis of Ethyl <i>N</i>-[(2-Boc-amino)ethyl]glycinate and Its Hydrochloride. Key Intermediates for Peptide Nucleic Acid Synthesis
  作者：Russell D. Viirre、Robert H. E. Hudson

  DOI：10.1021/jo026590w

  日期：2003.2.1

  An improved synthesis of ethyl N-[(2-Boc-amino)ethyl]glycinate and its hydrochloride salt is reported. The synthesis is based on the reductive alkylation of Boc-ethylenediamine with ethyl glyoxylate hydrate and furnishes the title compound in near quantitative yield and high purity without chromatography. This compound is suitable, as is, for the synthesis peptide nucleic acid monomers. Further, conversion

  据报道，N-[（2-Boc-氨基）乙基]甘氨酸乙酯及其盐酸盐的合成得到改进。该合成是基于Boc-乙二胺与乙醛酸乙酯水合物的还原烷基化，并且无需色谱即可以接近定量的收率和高纯度提供标题化合物。该化合物原样适合于合成肽核酸单体。此外，转化为盐酸盐提供了稳定的，不吸湿的固体，这是用于处理和储存的方便形式。