5-chloro-N,2-dimethoxy-N-methylbenzamide | 187396-78-7

• 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-chloro-N,2-dimethoxy-N-methylbenzamide
• 英文别名: N-methoxy-N-methyl-5-chloro-2-methoxybenzamide
• CAS: 187396-78-7
• 化学式: C₁₀H₁₂ClNO₃
• mdl: MFCD19106671
• 分子量: 229.663
• InChiKey: MBSPSQMYTSLAOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-chloro-N,2-dimethoxy-N-methylbenzamide 在 copper(l) iodide 、 四(三苯基膦)钯 、 正丁基锂 作用下， 以 乙醚 、 正己烷 、 乙腈 为溶剂， 反应 16.17h， 生成 3-(5-chloro-2-methoxybenzoyl)-5-methylbenzonitrile
  参考文献：
  名称：

  Structure−Activity Relationship Studies of Novel Benzophenones Leading to the Discovery of a Potent, Next Generation HIV Nonnucleoside Reverse Transcriptase Inhibitor

  摘要：

  Despite the progress of the past two decades, there is still considerable need for safe, efficacious drugs that target human immunodeficiency virus (HIV). This is particularly true for the growing number of patients infected with virus resistant to currently approved HIV drugs. Our high throughput screening effort identified a benzophenone template as a potential nonnucleoside reverse transcriptase inhibitor (NNRTI). This manuscript describes our extensive exploration of the benzophenone structure-activity relationships, which culminated in the identification of several compounds with very potent inhibition of both wild type and clinically relevant NNRTI-resistant mutant strains of HIV. These potent inhibitors include 70h (GW678248), which has in vitro antiviral assay IC50 values of 0.5 nM against wild-type HIV, 1 nM against the K103N mutant associated with clinical resistance to efavirenz, and 0.7 nM against the Y181C mutant associated with clinical resistance to nevirapine. Compound 70h has also demonstrated relatively low clearance in intravenous pharmacokinetic studies in three species, and it is the active component of a drug candidate which has progressed to phase 2 clinical studies.

  DOI：

  10.1021/jm050670l
• 作为产物：
  描述：

  5-氯-2-甲氧基苯甲酸 以93的产率得到5-chloro-N,2-dimethoxy-N-methylbenzamide
  参考文献：
  名称：

  Benzophenones as inhibitors of reverse transcriptase

  摘要：

  本发明涉及苯并酮化合物，其在抑制HIV逆转录酶方面具有用处，特别是在抑制其耐药品种方面。

  公开号：

  US06995283B2
• 作为试剂：
  描述：

  5-chloro-N,2-dimethoxy-N-methylbenzamide 、 1,3-二溴-5-氯苯 在 5-chloro-N,2-dimethoxy-N-methylbenzamide 作用下， 以97的产率得到(3-溴-5-氯苯基)-(5-氯-2-甲氧基苯基)甲酮
  参考文献：
  名称：

  J. Med. Chem. 2006, 49, 727-739

  摘要：

  DOI：

文献信息

• Alkynyl compounds as non nucleoside reverse transcriptase inhibitors
  申请人：Bonneau Pierre

  公开号：US20060069261A1

  公开（公告）日：2006-03-30

  Inhibitors of HIV reverse transcriptase which are useful for the treatment of HIV infection. Exemplars of the invention are compounds of the formula wherein the substituents are as defined in the following table. R 1 R 2 R 4 R 5 R 8a F CF 3 Me H —OH F CF 3 Cl H —OH F CF 3 Me H —O—CH 2 CO 2 H Cl CN Cl H —OH

  HIV逆转录酶抑制剂，用于治疗HIV感染。发明的示例是以下公式化合物，其中取代基如下表所定义。 R1 R2 R4 R5 R8a F CF3 Me H —OH F CF3 Cl H —OH F CF3 Me H —O—CH2CO2H Cl CN Cl H —OH
• Benzoic acid derivatives as non nucleoside reverse transcriptase inhibitors
  申请人：Simoneau Bruno

  公开号：US20060025480A1

  公开（公告）日：2006-02-02

  Compounds of formula (I): wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are as defined herein. The compounds are useful as reverse transcriptase inhibitors against HIV. In particular, the compounds are active against wild type and single or double mutant strains of HIV.

  式（I）的化合物：其中R1、R2、R3、R4、R5和R6如本文所定义。这些化合物可用作针对HIV的逆转录酶抑制剂。特别地，这些化合物对HIV的野生型和单个或双重突变株具有活性。
• 1,3,8-triaza- and 3,8-diaza-1-oxaspiro \x9b4,5! decane derivatives
  申请人：Syntex (U.S.A.) Inc.

  公开号：US05739336A1

  公开（公告）日：1998-04-14

  Heterocyclic compounds of Formula I: ##STR1## in which n is 2, 3, 4, 5 or 6; t is 1, 2, 3 or 4; u is 0 or 1 (provided that t is not 1 when u is 0); X is O or N(R.sup.4); Y and Z are independently C(O), C(S) or CH.sub.2 (provided that Y and Z are not both CH.sub.2); R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are as defined in the specification; and their pharmaceutically acceptable salts and N-oxides, formulations containing them, their uses as therapeutic agents, and their synthesis.

  公式I的杂环化合物：##STR1##其中n为2、3、4、5或6；t为1、2、3或4；u为0或1（前提是当u为0时，t不是1）；X为O或N(R.sup.4)；Y和Z独立地为C(O)、C(S)或CH.sub.2（前提是Y和Z不同时为CH.sub.2）；R.sup.1、R.sup.2、R.sup.3和R.sup.4如规范中所定义；以及它们的药学上可接受的盐和N-氧化物，含有它们的配方，它们作为治疗剂的用途，以及它们的合成。
• [EN] BENZOPHENONES AS INHIBITORS OF REVERSE TRANSCRIPTASE<br/>[FR] BENZOPHENONES AGISSANT COMME INHIBITEURS DE LA TRANSCRIPTASE INVERSE
  申请人：GLAXO GROUP LTD

  公开号：WO2001017982A1

  公开（公告）日：2001-03-15

  The present invention includes benzophenone compounds (I) which are useful in the treatment of HIV infections.

  本发明包括苯甲酮化合物（I），其在治疗HIV感染方面具有用处。
• Benzophenones as inhibitors of reverse transcriptase
  申请人：SmithKline Beecham Corporation

  公开号：US06995283B2

  公开（公告）日：2006-02-07

  The present invention is directed to beazophenone compounds useful in the inhibition of HIV reverse transcriptase, particularly its resistant varieties.

  本发明涉及苯并酮化合物，其在抑制HIV逆转录酶方面具有用处，特别是在抑制其耐药品种方面。