5-dimethylaminoisatoic anhydride | 77326-50-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 5-dimethylaminoisatoic anhydride
• 英文别名: 6-(dimethylamino)-1H-3,1-benzoxazine-2,4-dione
• CAS: 77326-50-2
• 化学式: C₁₀H₁₀N₂O₃
• 分子量: 206.201
• InChiKey: AXWIAWCOIXYGJJ-UHFFFAOYSA-N

物化性质

• 密度：
  1.336±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-dimethylaminoisatoic anhydride 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 ethyl 1,2-dihydro-4-hydroxy-1-methyl-6-(dimethylamino)-2-oxo-3-quinolinecarboxylate
  参考文献：
  名称：

  Synthesis and Biological Evaluation of New 1,2-Dihydro-4-hydroxy-2-oxo-3-quinolinecarboxamides for Treatment of Autoimmune Disorders:  Structure−Activity Relationship

  摘要：

  Roquinimex-related 3-quinolinecarboxamide derivatives were prepared and evaluated for treatment of autoimmune disorders. The compounds were tested in mice for their inhibitory effects on disease development in the acute experimental autoimmune encephalomyelitis model and selected compounds in the beagle dog for induction of proinflammatory reaction. Structure-activity relationships are discussed. Compound 8c, laquinimod, showed improved potency and superior toxicological profile compared to the lead compound roquinimex (1b, Linomide) and was selected for clinical studies (currently in phase II).

  DOI：

  10.1021/jm031044w
• 作为产物：
  描述：

  2-amino-5-dimethylamino-benzoic acid hydrochloride 、 N,N'-羰基二咪唑 以 乙二醇二甲醚 为溶剂， 反应 2.0h， 生成 5-dimethylaminoisatoic anhydride
  参考文献：
  名称：

  PROCESS FOR PRODUCTION OF PHENYLALANINE DERIVATIVES HAVING QUINAZOLINEDIONE SKELETONS AND INTERMEDIATES FOR THE PRODUCTION

  摘要：

  公开号：

  EP2103601B1

文献信息

• 2-氮杂芳基-6-取代氨基喹唑啉酮化合物及其制备方法和应用
  申请人：江西师范大学

  公开号：CN109503550B

  公开（公告）日：2022-11-29

  本发明公开了一类新型2‑氮杂芳基‑6‑取代氨基喹唑啉酮化合物及其制备方法和应用。本发明的2‑氮杂芳基‑6‑取代氨基喹唑啉酮化合物是一种荧光染料，可通过多种方法制备得到，其能够应用在单光子和双光子生物成像中。
• [EN] AMINOQUINOLINE DERIVATIVES AND THEIR USE AS ADENOSINE A3 LIGANDS<br/>[FR] DERIVES D'AMINOQUINOLINE ET LEUR UTILISATION COMME LIGANDS D'ADENOSINE A3
  申请人：SANOFI AVENTIS

  公开号：WO2005009969A1

  公开（公告）日：2005-02-03

  Compounds of the general formula (I), and their salts, solvates, isomers (tautomers, desmotrops, optically active isomers) as well as the salts and solvates; are strong adenosine A3 receptor ligands preferably antagonists.

  通式（I）的化合物及其盐、溶剂合物、同分异构体（互变异构体、去旋异构体、光学活性异构体）以及盐和溶剂合物；是强效的腺苷A3受体配体，最好是拮抗剂。
• Innately Water-Soluble Isatoic Anhydrides with Modulated Reactivities for RNA SHAPE Analysis
  作者：Adam B. Fessler、Abhishek Dey、Dominic S. Finis、Anthony J. Fowler、Kausik Chakrabarti、Craig A. Ogle

  DOI：10.1021/acs.bioconjchem.0c00024

  日期：2020.3.18

  2-methylnicotinic acid imidazolide (NAI) are two of the most commonly applied RNA-SHAPE electrophiles; 1M7 due to its high reactivity and NAI for its solubility and cell permeability. While the addition of a nitro group yields desirable activation of the reagent, it also leads to poorer water solubility. This limited solubility has motivated the development of water-soluble reagents. We present alternative

  1-甲基-7-亚硝基尿酸酐（1M7）和2-甲基烟酰胺基咪唑啉（NAI）是两种最常用的RNA-SHAPE亲电试剂。1M7具有高反应活性，NAI具有较高的溶解度和细胞渗透性。尽管添加硝基产生期望的试剂活化，但​​是它也导致较差的水溶性。这种有限的溶解度促进了水溶性试剂的开发。我们提出了具有可变反应性且同时可溶于水的替代品，基于等酸酐的试剂。通过使用季铵获得溶解性，而通过芳基环的官能化获得反应性的调节。讨论了试剂的合成，
• Aminoquinoline derivatives and their use as adenosine A3 ligands
  申请人：Aranyi Peter

  公开号：US20060211689A1

  公开（公告）日：2006-09-21

  The present invention relates to an adenosine A 3 receptor ligand of the general formula (I), within those preferably to the antagonists, including a salt, solvate or isomer (tautomer, desmotrop, and optically active isomer) thereof, to a pharmaceutical composition containing the ligand, to the use of the ligand, to its preparation, and intermediates of the ligand of the general formula (II″), (III″), (IV″), (V″), (VI″), (VII″), (VIII″) and (XIII″) and their preparation.

  本发明涉及一种通式(I)的腺苷A3受体配体，其中最好是拮抗剂，包括其盐、溶剂合物或异构体（互变异构体、去构异构体和光学活性异构体），以及含有该配体的制药组合物，该配体的使用，其制备以及通式(II"）、(III"）、(IV"）、(V"）、(VI"）、(VII"）、(VIII"）和(XIII"）的配体的中间体以及它们的制备。
• METHOD FOR PREPARING PHENYLALANINE DERIVATIVES HAVING QUINAZOLINE-DIONE SKELETON AND INTERMEDIATES FOR USE IN THE PREPARATION OF DERIVATIVES
  申请人：KATAOKA Noriyasu

  公开号：US20090318688A1

  公开（公告）日：2009-12-24

  A method for preparing a phenylalanine derivative having a quinazoline-dione ring represented by the following formula (1) or a pharmaceutically acceptable salt thereof, comprising the following steps (a), (b) and (c): (a) reacting an acyl phenylalanine derivative represented by the following formula (2): with a carbonyl group-introducing reagent and a specific anthranilic acid derivative to thus form the corresponding carboxy-asymmetric urea derivative; (b) converting the carboxy-asymmetric urea derivative into the corresponding quinazoline-dione derivative in the presence of a carboxyl group-activating agent: (c) if desired, substituting an N-alkyl group for the hydrogen atom bonded to the nitrogen atom present in the quinazoline-dione ring of the quinazoline-dione derivative using an N-alkylation agent and then deprotecting the resulting product, when the substituent R3′ which is a group corresponding to R3 is protected. According to this method, there can be obtained a phenylalanine derivative having a quinazoline-dione skeleton in a industrially favorably high yield.

  一种制备具有喹唑啉二酮环的苯丙氨酸衍生物或其药学上可接受的盐的方法，其由以下步骤(a)、(b)和(c)组成：(a)用羰基基团引入试剂和特定的蒽酸衍生物反应，以形成相应的羧基-不对称脲衍生物，所述脲衍生物由以下式(2)所表示的酰基苯丙氨酸衍生物反应而成：(b)在羧基活化剂的存在下，将羧基-不对称脲衍生物转化为相应的喹唑啉二酮衍生物；(c)如果需要，在R3'是被保护的基团对应的R3时，使用N-烷基化试剂将取代喹唑啉二酮环中氮原子上的氢原子的N-烷基基团替换，并去保护所得产物。根据该方法，可以得到一个工业上有利的高产率的具有喹唑啉二酮骨架的苯丙氨酸衍生物。