10-amino-9-fluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid | 86794-33-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 10-amino-9-fluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid
• 英文别名: 10-Amino-9-fluoro-2,3-dihydro-3-methyl-7-oxo-7h-pyrido [1,2,3-de]-1,4-benzoxazine-6-carboxylic acid；6-amino-7-fluoro-2-methyl-10-oxo-4-oxa-1-azatricyclo[7.3.1.05,13]trideca-5(13),6,8,11-tetraene-11-carboxylic acid
• CAS: 86794-33-4
• 化学式: C₁₃H₁₁FN₂O₄
• 分子量: 278.24
• InChiKey: RRDZXSXYSBGJCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  92.9
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  10-amino-9-fluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid 在 platinum(IV) oxide 、 sodium tetrahydroborate 、 四(三苯基膦)钯 、 乙醇 、 氢溴酸 、 氢气 、 sodium methylate 、 碳酸氢钠 、 溶剂黄146 、 sodium nitrite 作用下， 以 二氯甲烷 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 130.0 ℃ 、100.67 kPa 条件下， 反应 40.0h， 生成 11-[[[(3S)-1-(6-amino-3-pyridyl)-3-piperidyl]-[(2-methoxy-4-pyridyl)methyl]amino]methyl]-7-fluoro-2-methyl-6-(4-pyridyl)-4-oxa-1-azatricyclo[7.3.1.0^5,13]trideca-5(13),6,8,11-tetraen-10-one
  参考文献：
  名称：

  [EN] STIMULATOR OF INTERFERON GENES (STING) MODULATORS, AND COMPOSITIONS AND METHODS THEREOF
  [FR] MODULATEURS DE STIMULATEUR DE GÈNES D'INTERFÉRON (STING), ET COMPOSITIONS ET MÉTHODES ASSOCIÉES

  摘要：

  The invention provides novel modulators of STING (Stimulator of Interferon Genes) and pharmaceutical compositions thereof, as well as methods of their preparation and use, in therapy of various diseases and conditions, such as cancer, infectious and autoimmune diseases or disorders.

  公开号：

  WO2023158862A2
• 作为产物：
  描述：

  2-丙酮氧基-3,4-二氟硝基苯 在 盐酸 、 氨 、 氢气 、 镍 作用下， 以 乙醇 、 溶剂黄146 、 二甲基亚砜 为溶剂， 反应 7.0h， 生成 10-amino-9-fluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid
  参考文献：
  名称：

  Synthesis and antibacterial activities of substituted 7-oxo-2,3-dihydro-7H-pyrido(1,2,3-de)(1,4)benzoxazine-6-carboxylic acids.

  摘要：

  作为寻找新的合成抗菌剂以对抗全身感染的一部分，合成了多种7-氧代-2,3-二氢-7H-吡啶并[1,2,3-de][1,4]苯并噁嗪-6-羧酸类似物。在合成的新化合物中，9-氟-3-甲基-10-(4-甲基-1-哌嗪基)-7-氧代-2,3-二氢-7H-吡啶并[1,2,3-de][1,4]苯并噁嗪-6-羧酸（DL-8280）显示出对革兰氏阳性和阴性病原体，包括铜绿假单胞菌的强效抗菌活性，并且其代谢情况在单独的实验中显示为有利。

  DOI：

  10.1248/cpb.32.4907

文献信息

• Facile synthesis of carbon quantum dots loaded with mesoporous g-C₃N₄ for synergistic absorption and visible light photodegradation of fluoroquinolone antibiotics
  作者：Yingfei Wang、Fengliang Wang、Yiping Feng、Zhijie Xie、Qianxin Zhang、Xiaoyu Jin、Haijin Liu、Yang Liu、Wenying Lv、Guoguang Liu

  DOI：10.1039/c7dt04360k

  日期：——

  efficient charge separation of the CQDs. The eradication of FQs followed the Langmuir–Hinshelwood (L–H) kinetic degradation model and absorption pseudo-second-order kinetic model, indicating that surface reactions and chemical sorption played significant roles during the photocatalysis process. The results of electron spin resonance (ESR) technology and reactive species (RSs) scavenging experiments revealed

  迫切需要开发一种高效且有效的合成方法，以合成具有介孔gC 3 N 4（mpg-C 3 N 4 / CQDs）的碳量子点。在这里，开发了一种简便的策略，通过使用CQD，氰胺和二氧化硅胶体的混合物进行煅烧来合成mpg-C 3 N 4 / CQD。所获得的复合材料仍然保留了相当大的总表面积，可以提供更多的吸附位点。因此增强了氟喹诺酮类抗生素（FQs）的吸附能力。在可见光照射下，mpg-C 3 N 4/ CQDs对FQs的降解具有比本体gC 3 N 4或mpg-C 3 N 4更高的光催化活性。这种增强可能归因于mpg-C 3 N 4的高表面积，独特的上转换光致发光（PL）特性以及CQD的有效电荷分离。FQ的消除遵循了Langmuir-Hinshelwood（L-H）动力学降解模型和吸收伪二级动力学模型，这表明表面反应和化学吸附在光催化过程中起着重要作用。电子自旋共振（ESR）的技术和反应性物质（R
• Photoreactivity of biologically active compounds. XVIII. Photostability of ofloxacin in the solid state and in a tablet formulation
  作者：Tonnesen, Hanne Hjorth、Brunsvik、Loseth、Bergh、Gederaas

  DOI：10.1691/ph.2007.2.5184

  日期：——

  The photostability of ofloxacin in the solid state has been investigated. The change in colour of uncoated and film coated ofloxacin tablets and compressed ofloxacin was studied as a function of irradiance level and total exposure energy. The degradation of ofloxacin in the various preparations was quantified by HPLC and the antimicrobial activity was determined for selected tablets. The structure of two main degradation products from ofloxacin in the solid state has been postulated from LC-MS analysis. Both products have an absorption cut-off below 400 nm and cannot explain the observed change in tablet colour. There was no apparent relationship between the change in colour and the loss of active substance or antibacterial activity for the preparations investigated. The change in colour was easily detectable at rather low exposure levels. Apparently, there was a difference in light sensitivity between the two film-coated tablet batches investigated. The results obtained were partly dependent on the conditions within the radiation chamber (e.g. exposure time and irradiance level), which emphasizes the importance of testing the samples under various conditions unless the results are unequivocal. The tablets were sensitive to visible light although ofloxacin only has a neglectible absorption above 400 nm. The film coated ofloxacin tablets did, however, absorb above 400 nm with a cut-off at approximately 520 nm. A change in tablet coating to include a component that filters visible light in addition to UV radiation might provide a solution to the discolouration problem and prevent batch to batch variations with respect to light sensitivity.

  固态氧氟沙星的光稳定性已被研究。在不同的辐照水平和总曝光能量下，对未包衣和薄膜包衣的氧氟沙星片以及压制氧氟沙星的颜色变化进行了研究。通过高效液相色谱法量化了各制剂中氧氟沙星的降解程度，并测定了选定片剂的抗菌活性。根据液相色谱-质谱分析，推断出固态氧氟沙星的两个主要降解产物的结构。这两种产物在400纳米以下都有吸收截止，无法解释片剂颜色的变化。在研究的制剂中，颜色的变化与有效成分的损失或抗菌活性的丧失之间没有明显的关系。在相当低的曝光水平下，颜色的变化很容易被检测到。显然，在调查的两批发薄膜包衣片中，对光的敏感性存在差异。所得结果部分依赖于辐射室内的条件（例如曝光时间和辐照水平），这强调了在结果不明确时，在各种条件下测试样本的重要性。尽管氧氟沙星在400纳米以上的吸收可以忽略不计，但片剂对可见光敏感。然而，薄膜包衣的氧氟沙星片在约520纳米处有吸收截止。改变片剂包衣以包括一个过滤可见光和紫外线的成分，可能会解决褪色问题，并防止批次间关于光敏感性的变化。
• Nanopore enriched hollow carbon nitride nanospheres with extremely high visible-light photocatalytic activity in the degradation of aqueous contaminants of emerging concern
  作者：Yuxin Yang、An Hu、Xinyue Wang、Jiaqi Meng、Yihang Guo、Mingxin Huo、Suiyi Zhu

  DOI：10.1039/c8cy02073f

  日期：——

  Nanopore enriched hollow carbon nitride nanospheres exhibit extremely high visible-light photocatalytic activity in the degradation of aqueous contaminants of emerging concern.

  纳米孔富集的空心碳氮化物纳米球在降解新兴关注的水污染物方面表现出极高的可见光光催化活性。
• Adsorption-enhanced rapid catalytic degradation of ofloxacin by a CoS₂@montmorillonite catalyst <i>via</i> peroxymonosulfate activation
  作者：Peiping Hong、Lian Wu、Yifang Zhao、Yue Yu、Shuxi Gao、Bing Liao、Hao Pang

  DOI：10.1039/d2nj05913d

  日期：——

  With the combination of absorption capability and catalytic activity, the CoS2@MMT exhibited the potential as the AOP catalyst to degrade ofloxacin rapidly and effectively.

  CoS2@MMT 兼具吸收能力和催化活性，具有作为 AOP 催化剂快速有效降解氧氟沙星的潜力。
• Synthesis and evaluation of fluoroquinolone derivatives as substrate-based inhibitors of bacterial efflux pumps
  作者：Nadezhda German、Peng Wei、Glenn W. Kaatz、Robert J. Kerns

  DOI：10.1016/j.ejmech.2008.01.042

  日期：2008.11

  Bacterial efflux pump systems contribute to antimicrobial resistance in pathogenic bacteria. The co-administration of bacterial efflux pump inhibitors with antibiotics is being pursued to overcome efflux-mediated resistance to antibiotics. In this study we investigated a strategy for convening broad-spectrum efflux pump substrates, fluoroquinolone antibacterial agents which are inherently recognized by most efflux transporters, into expanded spectrum efflux pump inhibitors. Employing this strategy against organisms expressing efflux pumps from the MFS, MATE and RND classes of pump systems, we report here the identification of an ofloxacin-based EPI that is a potent inhibitor of MFS (NorA) and MATE (MepA) efflux pumps in Staphylococcus aureus. The methods described here outline a process that we feel will be broadly applicable to the systematic identification of bacterial efflux pump inhibitors. (C) 2008 Elsevier Masson SAS. All rights reserved.