6-溴甲基-2,3-二甲氧基-喹噁啉 | 69722-51-6

• 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: 6-溴甲基-2,3-二甲氧基-喹噁啉
• 英文名称: 6-(bromomethyl)-2,3-dimethoxyquinoxaline
• 英文别名: 6-Bromomethyl-2,3-dimethoxy-quinoxaline
• CAS: 69722-51-6
• 化学式: C₁₁H₁₁BrN₂O₂
• 分子量: 283.125
• InChiKey: LWUBGAGJHJXVDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  44.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-溴甲基-2,3-二甲氧基-喹噁啉 在 sodium hydroxide 、 cesium bicarbonate 、 水 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 4-((2,3-Dimethoxy-6-quinoxalinyl)methoxy)benzoic acid
  参考文献：
  名称：

  Quinoxaline chemistry Part 10. Quinoxaline 10-oxa-analogues of trimetrexate (TMQ ) and of 5,8-dideazafolic acid. Synthesis and evaluation of in vitro anticancer activity

  摘要：

  Among twenty-eight novel compounds (twenty-two 2,13-disubstituted-6-[(substituted-phenoxy)methyl-quinoxalines and six 4-[(2,3-disubstituted-quinoxalin-6-yl) methoxy]benzoylglutamates) only thirteen were selected at NCI for evaluation of their in vitro anticancer activity. The results have shown that compounds 3l,c,b,e and 4b were endowed with Significantly high values of percent tumor growth inhibition on several tumor cell lines at 10(-4) M, while compound 3t was characterized by a high selectivity, being still strongly inhibiting on three cell lines at 10(-5) M. Comparison of the presently observed activity with that of the previously described aza-analogues confirms that the effected isosteric substitution is highly valuable in some cases. (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(98)00003-2
• 作为产物：
  描述：

  2,3-二甲氧基-6-甲基-喹喔啉 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 16.0h， 以76%的产率得到6-溴甲基-2,3-二甲氧基-喹噁啉
  参考文献：
  名称：

  Quinoxaline chemistry Part 9. Quinoxaline analogues of trimetrexate (TMQ) and 10-propargyl-5,8-dideazafolic acid (CB 3717) and its precursors. Synthesis and evaluation of in vitro anticancer activity

  摘要：

  Eighteen quinoxalines bearing a methyleneanilino or methyleneaminobenzoylglutamate group on position 6 of the ring and various lipophilic substituents on positions 2 and 3 were prepared in order to discover if their structural analogy with both trimetrexate (TMQ) and 10-propargyl-5,8-dideazafolic acid (CB 3717) might display in vitro anticancer activity. Among these, 12 compounds were selected at the National Cancer Institute, Bethesda, MD, USA; they exhibited moderate (4b,d,i,l,m and 8) to strong (4f,h and 5a,e) cell-growth inhibition at a concentration of 10(-4) M. Interesting selectivities were also recorded between 10(-8) and 10(-6) M. These analogues proved to be less potent inihibitors of tumor cells than other classical and non-classical antifolate analogues previously described by us. (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(98)00002-0

文献信息

• Quinoxaline derivatives as new inhibitors of coxsackievirus B5
  作者：Antonio Carta、Giuseppina Sanna、Irene Briguglio、Silvia Madeddu、Gabriella Vitale、Sandra Piras、Paola Corona、Alessandra Tiziana Peana、Erik Laurini、Maurizio Fermeglia、Sabrina Pricl、Alessandra Serra、Elisa Carta、Roberta Loddo、Gabriele Giliberti

  DOI：10.1016/j.ejmech.2017.12.083

  日期：2018.2

  approved by the US Food and Drug Administration so far. Particularly, coxsackievirus infections have a worldwide distribution and can cause many important diseases. We here report the synthesis of new 14 quinoxaline derivatives and the evaluation of their cytotoxicity and antiviral activity against representatives of ssRNA, dsRNA and dsDNA viruses. Promisingly, three compounds showed a very potent and selective

  肠病毒是最常见和最重要的人类病原体之一，迄今为止，尚无美国食品和药物管理局批准的特定抗病毒药物。特别地，柯萨奇病毒感染在世界范围内分布并且可以引起许多重要的疾病。我们在这里报告了新的14种喹喔啉衍生物的合成及其对ssRNA，dsRNA和dsDNA病毒代表的细胞毒性和抗病毒活性的评估。令人信服的是，三种化合物对柯萨奇病毒B5表现出非常有效的选择性抗病毒活性，EC 50在亚微摩尔范围内（0.3-0.06μM）。实验技术（即杀病毒活性，药物添加时间和吸附测定的时间）和计算机技术的组合进行了进一步的建模研究，旨在了解最活跃，选择性最高且无细胞毒性的化合物4-[（（2,3-二甲氧基喹喔啉-6-基）甲硫基]乙基]乙酯的作用方式（6）。
• Aryl-quinazoline/aryl-2amino-phenyl methanone derivatives
  申请人：Altmann Eva

  公开号：US20060079685A1

  公开（公告）日：2006-04-13

  A compound of formula (I): wherein R1, R2, R3 and Y are as defined herein, or a pharmaceutically-acceptable and -cleavable ester, or acid addition salt thereof, useful for promoting the release of parathyroid hormone, e.g. for preventing or treating bone conditions which are associated with increased calcium depletion or resorption or in which stimulation of bone formation and calcium fixation in the bone is desirable.

  化合物的化学式为(I): 其中R1，R2，R3和Y的定义如下，或其药学上可接受和可水解酯或酸盐，用于促进甲状旁腺激素的释放，例如预防或治疗与钙流失或吸收增加或骨形成和钙固定在骨中有关的骨病情况。
• Aryl-quinazoline/aryl-2-amino-phenyl methanone derivatives
  申请人：Novartis AG

  公开号：US07696216B2

  公开（公告）日：2010-04-13

  A compound of formula (I): wherein R1, R2, R3 and Y are as defined herein, or a pharmaceutically-acceptable and -cleavable ester, or acid addition salt thereof, useful for promoting the release of parathyroid hormone, e.g. for preventing or treating bone conditions which are associated with increased calcium depletion or resorption or in which stimulation of bone formation and calcium fixation in the bone is desirable.

  化合物的公式（I）：其中R1，R2，R3和Y的定义如下，或其药学上可接受和可水解酯，或酸盐，有助于促进甲状旁腺激素的释放，例如用于预防或治疗与增加的钙耗竭或吸收有关的骨病状况，或者在其中骨形成和钙固定在骨中是可取的。
• Chinoxalinverbindungen, Verfahren zu deren Herstellung, deren Verwendung zum Weisstönen organischer Materialien und damit weissgetönte Materialien
  申请人：BAYER AG

  公开号：EP0000346A1

  公开（公告）日：1979-01-24

  Fluoreszenz-Farbstoffe der Formel worin X und Y Wasserstoff, Halogen, Alkyl, Aralkyl, Alkenyl, Hydroxy, Amino, Alkoxy, Arafkoxy, Cycloatkoxy, Aryloxy, Alkylmercapto, Alkylamino, Dialkylamino, Morpholino, Piperidino, Piperazino, Pyrrolidino, Acylamino oder Arylamino, Q Wasserstoff, Pyrazol-1-yl, Oxazol-2-yl, Benzoxazol-2-yl, Naphthoxazol-2-yl, 1,2,4-Oxadiazol-5-yl, 1,3,4-Oxadi- azol-2-yl, Isoxazol-3-yl, Isoxazol-5-yl, Thiazol-2-yl, Benz- thiazol-2-yl, 1,3,4-Thiadiazol-2-yl, Imidazol-2-yl, Benzimidazol-2-yl, 1,2,3-Triazol-2-yl, 1,2,3-Triazol-4-yl, 1,2,4-Triazol-3-yl, 1,2,4-Triazol-5-yl, 1,3,5-Triazin-2-yl, 2H-Benzotriazol-2-yl, 2H-Naphthotriazol-2-yl, 1,2,3,4-Tetrazol-5-yl, 1,2,3,4-Tetrazol-1-yl, Benzo[b]-furan-2-yl, Naphtho[2,1-b]-furan-2-yl, Benzo[b]-thiophon-2-yl, Naphtho[2,1-b]-thiophen-2-yl, Pyrimidin-2-yl, Pyridin-2-yl, Chinazolin-4-yl oder China- zolin-2-yl, und - für den Fall, dass n = 0 - auch Naphthyl, Stilben-4-yl, Benzo[b]-furan-6-yl, Dibenzofuran-3-yl, Di- benzofuran-2-yl, Chinoxalin-5-yl, Chinazolin-6-yl oder 2H-Benzotriazol-5-yl und n 0, 1 oder 2 bedeuten, wobei die Substituenten X, Y, Q und die übrigen cyclischen Reste durch für Weisstöner übliche nicht-chromophore Substituenten weiter substituiert sein können, eignen sich zum Weisstönen der verschiedensten synthetischen, halbsynthetischen und natürlichen organischen hochmolekularen Materialien.

  式中的荧光染料 式中 X和Y是氢、卤素、烷基、芳烷基、烯基、羟基、氨基、烷氧基、烷氧基、环烷氧基、芳氧基、烷基巯基、烷基氨基、二烷基氨基、吗啉基、哌啶基、哌嗪基、吡咯烷基、酰氨基或芳基氨基、 Q氢、吡唑-1-基、恶唑-2-基、苯并恶唑-2-基、萘并恶唑-2-基、1,2,4-噁二唑-5-基、1,3,4-噁二唑-2-基、异噁唑-3-基、异噁唑-5-基、噻唑-2-基、苯并噻唑-2-基、1,3、4-噻二唑-2-基、咪唑-2-基、苯并咪唑-2-基、1,2,3-三唑-2-基、1,2,3-三唑-4-基、1,2,4-三唑-3-基、1,2,4-三唑-5-基、1,3,5-三嗪-2-基、2H-苯并三唑-2-基、2H-萘并三唑-2-基、1,2,3、4-四唑-5-基、1,2,3,4-四唑-1-基、苯并[b]-呋喃-2-基、萘并[2,1-b]-呋喃-2-基、苯并[b]-噻吩-2-基、萘并[2,1-b]-噻吩-2-基、嘧啶-2-基、吡啶-2-基、喹唑啉-4-基或喹唑啉-2-基、在 n = 0 的情况下，还包括萘基、链烯-4-基、苯并[b]呋喃-6-基、二苯并呋喃-3-基、二苯并呋喃-2-基、喹喔啉-5-基、喹唑啉-6-基或 2H-苯并三唑-5-基，以及 n 为 0、1 或 2，其中取代基 X、Y、Q 和其他环状基可进一步被白色色调常用的非色素取代基取代、 适用于各种合成、半合成和天然有机高分子量材料的白色着色。
• Derivatives of aryl-quinazoline/aryl-2-amino-phenyl methanone which promote the release of parathyroid hormone
  申请人：Novartis Pharma AG

  公开号：EP1844780A2

  公开（公告）日：2007-10-17

  A compound of formula I wherein R1, R2, R3 and Y are as defined herein, or a pharmaceutically-acceptable and -cleavable ester, or acid addition salt thereof, useful for promoting the release of parathyroid hormone, e.g. for preventing or treating bone conditions which are associated with increased calcium depletion or resorption or in which stimulation of bone formation and calcium fixation in the bone is desirable.

  式 I 的化合物 其中 R1、R2、R3 和 Y 如本文所定义、 或其药学上可接受和可清除的酯或酸加成盐、 可用于促进甲状旁腺激素的释放，例如用于预防或治疗与钙消耗或吸收增加有关的骨病，或用于刺激骨形成和钙在骨中的固定。