ethyl 4-chloro-6,7,8-trifluoroquinoline-3-carboxylate | 207231-24-1

• 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: ethyl 4-chloro-6,7,8-trifluoroquinoline-3-carboxylate
• CAS: 207231-24-1
• 化学式: C₁₂H₇ClF₃NO₂
• mdl: MFCD09940895
• 分子量: 289.641
• InChiKey: WCFMOGCTVPWEFW-UHFFFAOYSA-N

物化性质

• 沸点：
  336.4±37.0 °C(Predicted)
• 密度：
  1.479±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 海关编码：
  2933499090

反应信息

• 作为反应物：
  描述：

  ethyl 4-chloro-6,7,8-trifluoroquinoline-3-carboxylate 在 二异丁基氢化铝 、 碳酸氢钠 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 26.0h， 生成 4-(4-fluorophenylthio)-6,7,8-trifluoroquinoline-3-methanol
  参考文献：
  名称：

  Development of a Practical and Efficient Synthesis of SIPI-4884, a HMG CoA Reductase Inhibitor for the Treatment of Hypercholesterolemia

  摘要：

  An improved process of the novel HMG CoA reductase inhibitor SIPI-4884 has been developed for early preclinical pharmacology and safety studies, and it was made up with an efficient nine-step and scalable process. Significant improvements in the nucleophilic substitution, reduction, Wittig-Horner reaction, and preparation of calcium salt were demonstrated. The overall yield was improved to 17.2%.

  DOI：

  10.1021/op400060z
• 作为产物：
  描述：

  6,7,8-三氟-1,4-二氢-4-氧代-3-喹啉羧酸乙酯 在 三氯氧磷 作用下， 反应 0.67h， 生成 ethyl 4-chloro-6,7,8-trifluoroquinoline-3-carboxylate
  参考文献：
  名称：

  高亲和力中央苯并二氮杂receptor受体配体：一系列新的吡唑并[4,3-c]喹啉-3-酮的合成与构效关系研究。

  摘要：

  制备了一系列在喹啉和N2-苯环上带有适当取代基的2-芳基（杂芳基）-2,5-二氢吡唑并[4,3-c]喹啉-3-（3H）-酮，并进行了测试。中央苯并二氮杂receptor受体配体。结构亲和关系研究的结果与先前提出的药效团模型完全吻合，此外，定量结构活性分析为高苯并二氮杂receptor受体亲和力的主要分子决定因素提供了更重要的见解。还确定并初步讨论了一些活性配体的内在活性。

  DOI：

  10.1016/s0968-0896(97)10039-6

文献信息

• THERAPEUTIC PYRAZOLOQUINOLINE DERIVATIVES
  申请人：Kaplan Alan P.

  公开号：US20080306049A1

  公开（公告）日：2008-12-11

  The invention provides a novel chemical series of formula I, as well as methods of use thereof for binding to the benzodiazepine site of the GABA A receptor and modulating GABA A , and use of the compound of formula I for the treatment of GABA A receptor associated disorders. The general structure of formula I is shown below and can exist in tautomeric forms: The invention further provides a method of modulation of one or more GABA A subtypes in an animal comprising administering to the animal an effective amount of a compound of formula (I).

  这项发明提供了一种新颖的化学系列，其化学式为I，以及用于结合到GABA A 受体的苯二氮卓类位点并调节GABA A 的使用方法，以及用于治疗与GABA A 受体相关疾病的化合物的使用。化学式I的一般结构如下所示，并且可以存在互变异构体形式： 该发明还提供了一种在动物中调节一个或多个GABA A 亚型的方法，包括向动物投与化学式(I)化合物的有效量。
• High affinity central benzodiazepine receptor ligands: synthesis and structure–activity relationship studies of a new series of pyrazolo[4,3- c ]quinolin-3-ones
  作者：L. Savini、P. Massarelli、C. Nencini、C. Pellerano、G. Biggio、A. Maciocco、G. Tuligi、A. Carrieri、N. Cinone、A. Carotti

  DOI：10.1016/s0968-0896(97)10039-6

  日期：1998.4

  tested as central benzodiazepine receptor ligands. Results from structure-affinity relationship studies were in full agreement with previously proposed pharmacophore models and, in addition, quantitative structure-activity analysis gave further significant insight into the main molecular determinants of high benzodiazepine receptor affinity. The intrinsic activity of some active ligands was also determined

  制备了一系列在喹啉和N2-苯环上带有适当取代基的2-芳基（杂芳基）-2,5-二氢吡唑并[4,3-c]喹啉-3-（3H）-酮，并进行了测试。中央苯并二氮杂receptor受体配体。结构亲和关系研究的结果与先前提出的药效团模型完全吻合，此外，定量结构活性分析为高苯并二氮杂receptor受体亲和力的主要分子决定因素提供了更重要的见解。还确定并初步讨论了一些活性配体的内在活性。
• Quinoline Compounds, Intermediates, Preparation Methods and Uses Thereof
  申请人：Cai Zhengyan

  公开号：US20110046379A1

  公开（公告）日：2011-02-24

  A kind of quinoline compounds as formula A, pharmaceutical accepted solvates, optical isomers or polymorphisms thereof. The intermediates of formula D. in which, R 1 , R 2 and R 3 is independently H, halo or the subustitents of formula H, in which, R is H, halo, C 1 ˜C 4 alkyl, C 1 ˜C 4 alkoxyl. The preparation methods and the uses for the manufacture of a medicament of inhibiting the HMG CoA reductase and treating the diseases relating to the high blood fat. Compared with the fluvastatin, rosuvatatin, pitavastatin disclosed in the prior arts, present quinoline compounds have better activity of inhibiting HMG CoA reductase. Present quinoline compounds can be used for treating the diseases relating to the high blood fat.

  一种喹啉类化合物，其化学式为A，药物可接受的溶剂化合物、光学异构体或其多晶形态。公式D的中间体。其中，R1、R2和R3独立地为H、卤素或公式H的取代基，其中，R为H、卤素、C1~C4烷基、C1~C4烷氧基。制备方法及用于制造抑制HMG CoA还原酶和治疗与高血脂相关疾病的药物的用途。与先前公开的氟伐他汀、罗伐他汀、匹伐他汀相比，目前的喹啉类化合物具有更好的抑制HMG CoA还原酶活性。目前的喹啉类化合物可用于治疗与高血脂相关的疾病。
• Synthesis and HMG CoA reductase inhibition of 4-thiophenyl quinolines as potential hypocholesterolemic agents
  作者：Zhengyan Cai、Weicheng Zhou、Lixin Sun

  DOI：10.1016/j.bmc.2007.08.044

  日期：2007.12

  8-trisubstituted-4-chloro-quinoline-3-carboxylates by several reactions and evaluated for their ability to inhibit the rat HMG CoA reductase in vitro. It was found that substitution with a variety of thiophenyl groups at position 4 in quinoline resulted in retention or enhancement of the inhibition and the preferable groups were 4-isopropyl-thiophenyl and 3-methoxy-thiophenyl. (4R,6S)-6-[(E)-2-(6,7,8-trifluoro-4

  由6,7,8-三取代-4-氯喹啉-3-羧酸乙酯经数个反应合成了一系列新颖的基于4-硫代苯基喹啉的甲羟戊酸内酯衍生物，并评估了它们在体外抑制大鼠HMG CoA还原酶的能力。 。发现在喹啉的4位上被各种硫代苯基取代会导致抑制作用的保持或增强，优选的基团是4-异丙基-硫代苯基和3-甲氧基-硫代苯基。（4R，6S）-6-[（E）-2-（6,7,8-三氟-4-异丙基硫代苯基-喹啉-3-基）-乙烯基]-3,4,5,6-四氢-4-羟基-2H-吡喃-2-酮（A16）和（4R，6S）-6-[（E）-2-（6-氟-4,7-二-（3-甲氧基-硫代苯基）-喹啉-3 -基）-乙烯基] -3,4，5，
• [EN] SUBSTITUTED QUINOLINE ANALOGS AS ALDEHYDE DEHYDROGENASE 1A1 (ALDH1A1) INHIBITORS<br/>[FR] ANALOGUES DE QUINOLÉINE SUBSTITUÉS UTILISÉS EN TANT QU'INHIBITEURS D'ALDÉHYDE DÉSHYDROGÉNASE 1A1 (ALDH1A1)
  申请人：US HEALTH

  公开号：WO2019089626A1

  公开（公告）日：2019-05-09

  The disclosure provides compounds of Formula I, which may be useful as aldehyde dehydrogenase inhibitors and the pharmaceutically acceptable salts thereof. The variables, J, R4, G, Q, and ring A are defined herein. Aldehyde dehydrogenase inhibitors of Formula I are useful for treating a variety of conditions including cancer and inflammation. The disclosure includes methods for using compounds and salts of Formula I to treat colon cancer, pancreatic cancer, nasopharyngeal carcinoma, thyroid cancer, prostate cancer, ovarian cancer, head and neck squamous cell carcinoma, lung cancer, hepatocellular carcinoma, leukemia, brain tumorsbreast cancer, atherosclerosis, ischaemic heart disease, acne vulgaris, asthma, autoimmune diseases, autoinflammatory diseases, chronic prostatitis, glomerulonephritis, inflammatory bowel disease, pelvic inflammatory disease, reperfusion injury, rheumatoid arthritis, sarcoidosis, transplant rejection, vasculitis, and interstitial cystitis. The disclosure also includes pharmaceutical compositions containing a compound or salt of Formula I.

  该披露提供了式I的化合物及其药物可接受的盐，可用作醛脱氢酶抑制剂。其中变量J，R4，G，Q和环A在此处定义。式I的醛脱氢酶抑制剂可用于治疗多种疾病，包括癌症和炎症。该披露包括使用式I的化合物和盐治疗结肠癌、胰腺癌、鼻咽癌、甲状腺癌、前列腺癌、卵巢癌、头颈部鳞状细胞癌、肺癌、肝细胞癌、白血病、脑肿瘤、乳腺癌、动脉粥样硬化、缺血性心脏病、痤疮、哮喘、自身免疫疾病、自身炎症性疾病、慢性前列腺炎、肾小球肾炎、炎症性肠病、盆腔炎症、再灌注损伤、类风湿性关节炎、结节病、移植排斥、血管炎和间质性膀胱炎的方法。该披露还包括含有式I的化合物或盐的制药组合物。