5-[(2-Chloro-phenylamino)-methylene]-2,2-dimethyl-[1,3]dioxane-4,6-dione | 383895-05-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-[(2-Chloro-phenylamino)-methylene]-2,2-dimethyl-[1,3]dioxane-4,6-dione
• 英文别名: 5-{[(2-Chlorophenyl)amino]methylidene}-2,2-dimethyl-1,3-dioxane-4,6-dione；5-[(2-chloroanilino)methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione
• CAS: 383895-05-4
• 化学式: C₁₃H₁₂ClNO₄
• mdl: MFCD02936585
• 分子量: 281.696
• InChiKey: JKRDXRQPIMCMIM-UHFFFAOYSA-N

物化性质

• 沸点：
  474.6±45.0 °C(Predicted)
• 密度：
  1.433±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-[(2-Chloro-phenylamino)-methylene]-2,2-dimethyl-[1,3]dioxane-4,6-dione 反应 2.0h， 以75%的产率得到8-氯-4-羟基喹啉
  参考文献：
  名称：

  一种新型的离子液体介导的4（1 H）-喹诺酮，5 H-噻唑并[3,2- a ]嘧啶-5-酮和4 H-嘧啶并[2,1- b ]苯并噻唑-4-酮的合成

  摘要：

  一种新的，方便的，环境友好的两步合成4（1 H）-喹诺酮，5 H-噻唑并[3,2- a ]嘧啶-5-酮和4 H-嘧啶并[2,1- b ]苯并噻唑-通过先在中等温度下将取代的芳基胺/ 2-氨基噻唑/ 2-氨基苯并噻唑与Meldrum的酸和原甲酸三甲酯在1-丁基-3-甲基咪唑鎓溴化物中在中等温度下缩合，得到5-{（取代的芳基/ 4-甲基噻唑基/取代的苯并噻唑基）亚甲基} -2，2-二甲基-1，3-二恶烷-4，6-二酮。在中等温度下在1-丁基-3-甲基四氟硼酸酯/三氟甲磺酸酯中环化后得到的化合物以优异的收率得到标题化合物。

  DOI：

  10.1016/j.tetlet.2011.12.024
• 作为产物：
  描述：

  丙二酸环(亚)异丙酯 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 5-[(2-Chloro-phenylamino)-methylene]-2,2-dimethyl-[1,3]dioxane-4,6-dione
  参考文献：
  名称：

  Synthesis of ring-substituted 4-aminoquinolines and evaluation of their antimalarial activities

  摘要：

  A simple two-step synthesis method was used to make 51 B-ring-substituted 4-hydroxyquinolines allowing analysis of the effect of ring substitutions on inhibition of growth of chloroquine sensitive and resistant strains of Plasmodium falciparum, the dominant cause of malaria morbidity. Substituted quinoline rings other than the 7-chloroquinoline ring found in chloroquine were found to have significant activity against the drug-resistant strain of P. falciparum W2. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.037

文献信息

• [EN] HEPATITIS C INHIBITOR PEPTIDE ANALOGS<br/>[FR] ANALOGUES PEPTIDIQUES D'INHIBITEURS DE L'HEPATITE C
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2006000085A1

  公开（公告）日：2006-01-05

  The invention relates to compounds of formula (I) wherein R', R2, R3, R4, R5, R6, Y, n and m are as defined herein. The compounds are useful for the treatment and prevention of hepatitis C viral infections in mammals by inhibiting HCV NS3 protease. The invention further relates to azalactone compounds of the formula (III) which can be reacted with an amide anion to produce the compounds of formula (I).

  本发明涉及式(I)的化合物，其中R'，R2，R3，R4，R5，R6，Y，n和m如本文所述定义。这些化合物通过抑制HCV NS3蛋白酶，用于治疗和预防哺乳动物中的丙型肝炎病毒感染。本发明进一步涉及可以与酰胺阴离子反应以产生式(I)化合物的azalactone化合物（III）。
• [EN] HEPATITIS C INHIBITOR DIPEPTIDE ANALOGS<br/>[FR] ANALOGUES DIPEPTIDIQUES D'INHIBITEURS DE L'HEPATITE C
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2006007700A1

  公开（公告）日：2006-01-26

  The present invention relates to compounds of formula (I): wherein R1, R2, R4, n and m are as defined herein and R3 is selected from: (i) -C(O)OR31 wherein R31 is (C1-6)alkyl or aryl, wherein the (C1-6)alkyl is optionally substituted with one to three halogen substituents; (ii) -C(O)NR32R33, wherein R32 and R33 are each independently selected form H, (C1-6)alkyl, and Het; (iii) -SOvR34, wherein v is 1 or 2 and R34 is selected from: (C1-6)alkyl, aryl, Het, and NR32R33 wherein R32 and R33 are as defined above; and (iv) -CO(O)-R35, wherein R35 is selected from (C1-8)alkyl, (C3-7)cycloalkyl-(C1-4)alkyl, aryl, aryl-(C1-6)alkyl, Het and Het-(C1-6)alkyl, each of which are optionally substituted with one or more substituents each independently selected from halo, (C1-6)alkyl, (C3-7)cycloalkyl, aryl, Het, hydroxyl, -O-(C1-6)alkyl, -S-(C1-6)alkyl, -SO-(C1-6)alkyl, -SO2-(C1-6)alkyl, -O-aryl, -S-aryl, -SO-aryl and -SO2-aryl, wherein the aryl portion of the -O-aryl, -S-aryl, -SO-aryl and -SO2-aryl are each optionally substituted with one to five halo substituents. The present invention further relates to pharmaceutical compositions containing the compounds of formula (I) and methods for using these analogs in the treatment of HCV infection.

  本发明涉及以下式(I)的化合物：其中R1、R2、R4、n和m如本文所定义，R3选自：(i)-C(O)OR31，其中R31为(C1-6)烷基或芳基，其中(C1-6)烷基可选择地用一到三个卤素取代基取代；(ii)-C(O)NR32R33，其中R32和R33各自独立地选自H、(C1-6)烷基和Het；(iii)-SOvR34，其中v为1或2，R34选自：(C1-6)烷基、芳基、Het和NR32R33，其中R32和R33如上所定义；和(iv)-CO(O)-R35，其中R35选自(C1-8)烷基、(C3-7)环烷基-(C1-4)烷基、芳基、芳基-(C1-6)烷基、Het和Het-(C1-6)烷基，每种均可选择地用一种或多种取代基取代，每种取代基各自独立地选自卤素、(C1-6)烷基、(C3-7)环烷基、芳基、Het、羟基、-O-(C1-6)烷基、-S-(C1-6)烷基、-SO-(C1-6)烷基、-SO2-(C1-6)烷基、-O-芳基、-S-芳基、-SO-芳基和-SO2-芳基，其中-O-芳基、-S-芳基、-SO-芳基和-SO2-芳基的芳基部分可选择地用一到五个卤素取代基取代。本发明还涉及含有式(I)化合物的药物组合物以及在治疗HCV感染中使用这些类似物的方法。
• Hepatitis C inhibitor peptide analogs
  申请人：Bailey D. Murray

  公开号：US20060019905A1

  公开（公告）日：2006-01-26

  Compounds of formula (I): wherein R 1 , R 2 , R 3 , R 4 , R 5 , Y, n and m are as defined herein. The compounds are useful as inhibitors of HCV NS3 protease.

  式（I）的化合物：其中R1、R2、R3、R4、R5、Y、n和m的定义如本文所述。这些化合物可用作HCV NS3蛋白酶的抑制剂。
• A one-pot, two-step synthesis of 3-deazacanthin-4-ones via sequential Pd-catalyzed Suzuki-Miyaura and Cu-catalyzed Buchwald-Hartwig reactions
  作者：Emmanouil Broumidis、Panayiotis A. Koutentis

  DOI：10.1016/j.tetlet.2017.05.076

  日期：2017.7

  yields from 8-iodoquinolones and 2-chloro(het)arylboronic acids. The strategy involves construction of the central B ring via concomitant Pd-catalyzed Suzuki-Miyaura CC and Cu-catalyzed Buchwald-Hartwig CN coupling reactions.

  从8-碘喹诺酮和2-氯（杂）芳基硼酸快速制备了3-Deazantanthin-4-one和9个类似物，包括8-aza类似物。该策略涉及通过伴随的Pd催化的Suzuki-Miyaura C C和Cu催化的Buchwald-Hartwig C N偶联反应来构建中心B环。
• MACROCYCLIC PEPTIDES ACTIVE AGAINST THE HEPATITIS C VIRUS
  申请人：LLINAS-BRUNET Montse

  公开号：US20090264346A1

  公开（公告）日：2009-10-22

  Compounds of formula (I): wherein R 1 , R 2 , X, R 3 , D, and the dotted line b are as defined herein; or a pharmaceutically acceptable salt or ester thereof, are useful as inhibitors of the HCV NS3 protease.

  式(I)的化合物：其中R1，R2，X，R3，D和虚线b的定义如本文所述；或其药学上可接受的盐或酯，可用作HCV NS3蛋白酶的抑制剂。