3-吡啶羧酸,4-氯-5-乙基-1,2-二氢-6-甲基-2-羰基-,乙基酯 | 172469-74-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 3-吡啶羧酸,4-氯-5-乙基-1,2-二氢-6-甲基-2-羰基-,乙基酯
• 英文名称: 3-carbethoxy-4-chloro-5-ethyl-6-methyl-2(1H)-pyridinone
• 英文别名: 4-chloro-5-ethyl-6-methyl-3-carbethoxypyridin-2(1H)-one；ethyl 4-chloro-5-ethyl-6-methyl-2-oxo-1H-pyridine-3-carboxylate
• CAS: 172469-74-8
• 化学式: C₁₁H₁₄ClNO₃
• 分子量: 243.69
• InChiKey: ZHHICFKRQARFCK-UHFFFAOYSA-N

物化性质

• 沸点：
  364.7±42.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-吡啶羧酸,4-氯-5-乙基-1,2-二氢-6-甲基-2-羰基-,乙基酯 在 盐酸 、 硝酸 、 溶剂黄146 、 tin(ll) chloride 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 3-amino-4-(3,5-dimethylphenoxy)-5-ethyl-6-methyl-1H-pyridin-2-one
  参考文献：
  名称：

  3-Iodo-4-phenoxypyridinones (IOPY's), a new family of highly potent non-nucleoside inhibitors of HIV-1 reverse transcriptase

  摘要：

  Building upon the potent anti-HIV-1 activities observed for the 3-dimethylamino-4-benzylpyridinone 2, and the corresponding 4-aryloxypyridinone analogue 3, a concise and efficient route to the 3-iodo-4-aryloxypyridinones 14a-c (IOPY's) was developed. This involved reaction of the 4-hydroxy substituted pyridinone 10 with the requisite dichloroiodobenzene reagent 11. IOPY compound 14c is active at IC50 = 1-45 nM against wild type HIV-1 and a panel of six major simple/double HIV mutant strains. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.045
• 作为产物：
  描述：

  2-乙基乙酰乙酸乙酯 在 硝酸铵 、 苄基三乙基氯化铵 、 sodium ethanolate 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙醇 、 乙腈 为溶剂， 反应 198.5h， 生成 3-吡啶羧酸,4-氯-5-乙基-1,2-二氢-6-甲基-2-羰基-,乙基酯
  参考文献：
  名称：

  A New Series of Pyridinone Derivatives as Potent Non-Nucleoside Human Immunodeficiency Virus Type 1 Specific Reverse Transcriptase Inhibitors

  摘要：

  4-(Arylthio)-pyridin-2(1H)-ones variously substituted in their 3-, 5-, and 6-positions have been synthesized as a new series of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT)-pyridinone hybrid molecules. Biological studies revealed that some of them show potent HIV-1 specific reverse transcriptase inhibitory properties. Compounds 16 and 7c, the most active ones, inhibit the replication of HIV-1 at 3 and 6 nM, respectively.

  DOI：

  10.1021/jm00023a007

文献信息

• 4-Aryl-thio-pyridin-2(1H)-ones, medicines containing them and their uses
  申请人：Centre National de la Recherche Scientifique (CNRS)

  公开号：US06015820A1

  公开（公告）日：2000-01-18

  Compounds of formula (3) in which: R.sub.1 and R.sub.2 independently represent an atom of hydrogen, an aliphatic group or an alkyloxyalkyl group in which the alkyl chains are from C.sub.1 to C.sub.4 or together form an aromatic ring; R.sub.3 represents: an atom of hydrogen, or an NHR.sub.5 group in which R.sub.5 represents an atom of hydrogen or a COR.sub.6 group in which R.sub.6 is an aliphatic or aromatic group, or an NO.sub.2 group or a COOR.sub.7 group in which R.sub.7 is an aliphatic group, R.sub.4 represents a phenyl or heterocyclic group. These compounds can be used in the treatment of illnesses linked to the HIV virus.

  式（3）中的化合物，其中：R.sub.1和R.sub.2分别表示氢原子、脂肪基或烷氧基烷基，其中烷基链为C.sub.1到C.sub.4，或者一起形成芳香环；R.sub.3表示：氢原子，或者NHR.sub.5基团，其中R.sub.5表示氢原子或者COR.sub.6基团，其中R.sub.6是脂肪基或芳香基，或者NO.sub.2基团或COOR.sub.7基团，其中R.sub.7是脂肪基，R.sub.4表示苯基或杂环基团。这些化合物可用于治疗与HIV病毒相关的疾病。
• Structure–activity relationship in the 3-iodo-4-phenoxypyridinone (IOPY) series: The nature of the C-3 substituent on anti-HIV activity
  作者：Abdellah Benjahad、Said Oumouch、Jerôme Guillemont、Elisabeth Pasquier、Dominique Mabire、Koen Andries、Chi Hung Nguyen、David S. Grierson

  DOI：10.1016/j.bmcl.2006.10.082

  日期：2007.2

  As part of a systematic SAR study on the 3-iodo-4-phenoxypyridinone 3 (IOPY) type non-nucleoside reverse transcriptase inhibitors, the analogues 4a-4z bearing different C-3 substituents were synthesized and evaluated for their anti-HIV activity against wild-type HIV-1 and four of the principal HIV mutant strains (K103N, Y181C, Y188L, and 1100L). The results show that the 3-vinyl analogue 4j is the only compound which displays anti-HIV activity comparable to IOPY 3, and in this respect represents a possible back-up to this lead molecule. (c) 2006 Elsevier Ltd. All rights reserved.
• 4-ARYL-THIO-PYRIDIN-2(1H)-ONES, MEDICAMENTS LES CONTENANT ET LEURS UTILISATIONS DANS LE TRAITEMENT DE MALADIES LIEES AUX VIH
  申请人：CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE

  公开号：EP0843663B1

  公开（公告）日：2003-04-09
• US6015820A
  申请人：——

  公开号：US6015820A

  公开（公告）日：2000-01-18
• [EN] 4-ARYL-THIO-PYRIDIN-2(1H)-ONES, DRUGS CONTAINING SAME, AND USES THEREOF FOR TREATING HIV-RELATED DISEASES<br/>[FR] 4-ARYL-THIO-PYRIDIN-2(1H)-ONES, MEDICAMENTS LES CONTENANT ET LEURS UTILISATIONS DANS LE TRAITEMENT DE MALADIES LIEES AUX VIH
  申请人：CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE

  公开号：WO1997005113A1

  公开（公告）日：1997-02-13

  (EN) Compounds of formula (3), wherein each of R1 and R2, which are the same or different, is a hydrogen atom, an aliphatic group or an alkyloxyalkyl group in which the alkyl chains have 1-4 carbon atoms or together form an aromatic ring; R3 is a hydrogen atom or a group NHR5 where R5 is a hydrogen atom or a group COR6 where R6 is an aliphatic or aromatic group, or a group NO2, or a group COOR7 where R7 is an aliphatic group; and R4 is a phenyl group or heterocycle. Said compounds may be used for treating HIV-related diseases.(FR) Composés de formule (3) dans laquelle: R1 et R2 représentent indépendamment un atome d'hydrogène, un groupe aliphatique ou un groupe alkyloxyalkyle dans lequel les chaînes alkyle sont en C1 à C4, ou forment ensemble un cycle aromatique; R3 représente: un atome d'hydrogène, ou un groupe NHR5 dans lequel R5 représente un atome d'hydrogène ou un groupe COR6 dans lequel R6 est un groupe aliphatique ou aromatique, ou un groupe NO2 ou un groupe COOR7 dans lequel R7 est un groupe aliphatique, R4 représente un groupe phényle ou un hétérocycle. Ces composés peuvent être utilisés dans le traitement de maladies liées au virus VIH.