4-[2-(6,7-二甲氧基-4-甲基-3-氧代-3,4-二氢-喹喔啉-2-基)-乙基]-[1,2,4]三氮唑-3,5-二酮 | 132788-52-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 4-[2-(6,7-二甲氧基-4-甲基-3-氧代-3,4-二氢-喹喔啉-2-基)-乙基]-[1,2,4]三氮唑-3,5-二酮
• 英文名称: 4-[2-(6,7-dimethoxy-4-methyl-3-oxo-3,4-dihydroquinoxalinyl)ethyl]-1,2,4-triazoline-3,5-dione
• 英文别名: 4-<2-(6,7-dimethoxy-4-methyl-3-oxo-3,4-dihydroquinoxalyl)ethyl>-1,2,4-triazoline-3,5-dione；4-[2-(6,7-dimethoxy-4-methyl-3-oxo-3,4-dihydroquinoxalyl)ethyl]-1,2,4-triazoline-3,5-dione；4-[2-(3,4-dihydro-6,7-dimethoxy-4-methyl-3-oxo-2-quinoxalinyl)ethyl]-3H-1,2,4-triazole-3,5(4H)-dione；DMEQ-TAD；4-[2-(6,7-dimethoxy-4-methyl-3-oxoquinoxalin-2-yl)ethyl]-1,2,4-triazole-3,5-dione
• CAS: 132788-52-4
• 化学式: C₁₅H₁₅N₅O₅
• 分子量: 345.315
• InChiKey: NPKSULYVSICWLD-UHFFFAOYSA-N

物化性质

• 熔点：
  >200?C (dec.)
• 沸点：
  533.5±60.0 °C(Predicted)
• 密度：
  1.52±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（轻微）、DMSO（轻微）、乙酸乙酯（轻微、加热）

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  9-顺式维甲酸 、 4-[2-(6,7-二甲氧基-4-甲基-3-氧代-3,4-二氢-喹喔啉-2-基)-乙基]-[1,2,4]三氮唑-3,5-二酮 以 二氯甲烷 为溶剂， 反应 1.0h， 以60%的产率得到
  参考文献：
  名称：

  Reaction of geometrical isomers of retinoic acid with 1,2,4-triazoline-3,5-dione having fluorescent chromophore

  摘要：

  Reactions of 1,2,4-triazoline-3,5-dione having fluorescent chromophore (DMEQ-TAD) with 9Z-, 11Z-, 13Z-, and 11Z,13Z-isomers of retinoic acid were studied. Except for the 9Z-isomer, the reactions gave the 7,10-adducts in high selectivity while 9Z-isomer gave only the 5,8,11,14-bis adducts. Interesting self-sensitized photochemical isomerizations of these adducts and the mechanism of the addition reactions ant discussed.

  DOI：

  10.1016/s0040-4039(00)73195-9
• 作为产物：
  描述：

  1,2-二氨基-4,5-二甲氧基苯 在 碘苯二乙酸 、 二苯基膦叠氮化物 、 potassium carbonate 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 7.5h， 生成 4-[2-(6,7-二甲氧基-4-甲基-3-氧代-3,4-二氢-喹喔啉-2-基)-乙基]-[1,2,4]三氮唑-3,5-二酮
  参考文献：
  名称：

  Synthesis of highly fluorescent dienophiles for detecting conjugated dienes in biological fluid

  摘要：

  具有高荧光取代基的氟源二烯亲体，1,2,4-三氮唑-3,5-二酮衍生物1a、b被合成作为检测带有共轭二烯基的生物化合物的试剂。

  DOI：

  10.1039/c39900001416

文献信息

• Reaction of vitamin A with 1,2,4-triazoline-3,5-diones
  作者：Sachiko Yamada、Kazuhiko Hamano、Masato Shimizu、Hiroshi Ichikawa

  DOI：10.1016/s0040-4039(00)79928-x

  日期：1991.5

  Vitamin A and its metabolites reacted with 1,2,4-triazoline-3,5-diones to give 11,14- (retinol) or 7,10-adduct (retinal and retinoic acid) with high regioselectivity depending on the nature of the terminal functional group. The regioselectivity of the reaction was discussed incompared with that with singlet oxygen.

  维生素A及其代谢物与1,2,4-三唑啉-3,5-二酮反应生成11,14-（视黄醇）或7,10-加合物（视黄酸和视黄酸），视其性质而定终端功能组。与单线态氧相比，讨论了反应的区域选择性。
• Effect of carbon chain length in acyl coenzyme A on the efficiency of enzymatic transformation of okadaic acid to 7- O -acyl okadaic acid
  作者：Sachie Furumochi、Tatsuya Onoda、Yuko Cho、Haruhiko Fuwa、Makoto Sasaki、Mari Yotsu-Yamashita、Keiichi Konoki

  DOI：10.1016/j.bmcl.2016.05.027

  日期：2016.7

  Saturated fatty acyl CoAs with a carbon chain length of 14, 16 and 18 exhibited higher yields than those with a carbon chain length of 10 or 12. Acyl CoAs with carbon chain lengths from 14 to 18 and containing either a diene unit, an alkyne unit, or an azide unit in the carbon chain were synthesized and shown to provide the corresponding DTX3 with a yield comparable to that of hexadecanoyl CoA. The three

  冈果酸（原鞭毛原鞭毛体物种的产物）在各种双壳类动物中被转化为7- O-酰基OA。在存在来自双壳类动物消化腺的微粒体级分的情况下，结构转化在体外以酶促方式进行。我们一直在使用LC-MS / MS通过检测7- O来鉴定OA转化酶-酰基OA，也称为dinophysistoxin 3（DTX3）。但是，由于OA转化酶是一种膜蛋白，而DTX3的替代测定是必需的，而溶解膜蛋白的表面活性剂会降低LC-MS / MS的灵敏度。本研究研究了饱和脂肪酰基CoA，其碳链长度为10（癸酰基），12（十二烷酰基），14（十四烷酰基），16（十六烷酰基）和18（十八烷酰基）为体外酰化反应的底物。碳链长度为14、16和18的饱和脂肪酰基CoA的收率高于碳链长度为10或12的饱和脂肪酰基CoA。碳链长度为14至18且包含二烯单元，炔烃单元的酰基CoA ，合成或显示出碳链中的叠氮单元或叠氮化物单元，并显示出可提供与十六烷酰
• Simultaneous Determination of 25-Hydroxyvitamin D2 and 25-Hydroxyvitamin D3 in Human Plasma by Liquid Chromatography-Tandem Mass Spectrometry Employing Derivatization with a Cookson-Type Reagent.
  作者：Tatsuya HIGASHI、Daisuke AWADA、Kazutake SHIMADA

  DOI：10.1248/bpb.24.738

  日期：——

  A rapid and highly sensitive LC-MS-MS method for simultaneous determination of 25-hydroxyvitamin D2 [25(OH)D2] and 25-hydroxyvitamin D3 [25(OH)D3] in human plasma has been developed using derivatization with a Cookson-type reagent, 4-[2-(6,7-dimethoxy-4-methyl-3-oxo-3,4-dihydroquinoxalyl)ethyl]-1,2,4-triazoline-3,5-dione (DMEQTAD). The derivatization with DMEQTAD significantly improved the ionization efficiencies of 25(OH)D2 and 25(OH)D3 with detection limits of 20 and 12.5 fmol (8 and 5 pg) per injection, respectively. The method employed two steps of solvent extraction but did not require chromatographic purifications for sample pretreatment. The determination was carried out by mass chromatography of the protonated molecular ions formed by atmospheric pressure chemical ionization operating in the positive-ion mode after the derivatization, and 25-hydroxyvitamin D4 was used as an internal standard. The intra-assay coefficients of variation were below 4.02 and 3.24% for 25(OH)D2 and 25(OH)D3, respectively, and the analytical recoveries of both compounds were quantitative. Assay linearity was obtained in the range of 0.05—1 ng per tube and the determination limit was 3 ng/ml for a 20 μl plasma aliquot, for each compound. The developed method was applied to plasma samples obtained from volunteers, two of whom had received vitamin D2 supplementation, and gave satisfactory results.

  开发了一种快速、高灵敏度的 LC-MS-MS 方法，可使用 Cookson-衍生化方法同时测定人血浆中的 25-羟基维生素 D2 [25(OH)D2] 和 25-羟基维生素 D3 [25(OH)D3]。型试剂，4-[2-(6,7-二甲氧基-4-甲基-3-氧代-3,4-二氢喹喔啉基)乙基]-1,2,4-三唑啉-3,5-二酮(DMEQTAD)。使用 DMEQTAD 衍生化显着提高了 25(OH)D2 和 25(OH)D3 的电离效率，每次进样的检测限分别为 20 和 12.5 fmol（8 和 5 pg）。该方法采用两步溶剂萃取，但样品预处理不需要色谱纯化。采用衍生化后以正离子模式操作的常压化学电离形成的质子化分子离子质谱进行测定，以25-羟基维生素D4作为内标。 25(OH)D2 和 25(OH)D3 的测定内变异系数分别低于 4.02 和 3.24%，并且两种化合物的分析回收率都是定量的。对于每种化合物，测定线性范围为每管 0.05-1 ng，20 μl 血浆等分试样的测定限为 3 ng/ml。所开发的方法应用于从志愿者（其中两名补充了维生素 D2）获得的血浆样本，并得到了令人满意的结果。
• Exploiting furan's versatile reactivity in reversible and irreversible orthogonal peptide labeling
  作者：Kurt Hoogewijs、Dieter Buyst、Johan M. Winne、José C. Martins、Annemieke Madder

  DOI：10.1039/c3cc40588e

  日期：——

  A general method for the facile and versatile decoration of peptides is proposed exploiting furan based cycloaddition and electrophilic aromatic substitution reactions. Given the commercial availability of furylalanine derivatives for peptide synthesis, the current work significantly enlarges the toolbox of available methodologies for site specific labeling and conjugation of peptide probes.

  利用基于呋喃的环加成和亲电子芳族取代反应，提出了一种用于肽的简便且通用的修饰的通用方法。考虑到呋喃丙氨酸衍生物在商业上可用于肽合成，当前的工作大大扩大了用于肽探针的位点特异性标记和缀合的可用方法的工具箱。
• Fluorometric Measurement of Yessotoxins in Shellfish by High-pressure Liquid Chroraatography
  作者：Takeshi Yasumoto、Azusa Takizawa

  DOI：10.1271/bbb.61.1775

  日期：1997.1

  A rapid HPLC method with fluorescence detection of yessotoxin (YTX) and its two analogs (45-OHYTX and norYTX) in mussels and scallops is presented. A dienophile reagent, DMEQ-TAD, was used for fluorescence labeling. YTX was measured in the range 1–100 ng. The method confirmed the occurrence of YTX and 45-OHYTX for the first time in mussels from Chile and New Zealand

  本文介绍了一种快速高效液相色谱法，用于检测贻贝和扇贝中的耶索毒素（YTX）及其两种类似物（45-OHYTX和norYTX）。使用二烯亲试剂DMEQ-TAD进行荧光标记。YTX的测量范围为1-100 ng。该方法首次证实了智利和新西兰贻贝中存在YTX和45-OHYTX。