4-{(2-pyridinylmethyl)thio}azetidin-2-one | 187815-13-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 4-{(2-pyridinylmethyl)thio}azetidin-2-one
• 英文别名: 4-(Pyridin-2-ylmethylsulfanyl)azetidin-2-one
• CAS: 187815-13-0
• 化学式: C₉H₁₀N₂OS
• 分子量: 194.257
• InChiKey: ZTGRLHMTZBGQKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  67.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-(+)-1-苯乙基异氰酸酯 、 4-{(2-pyridinylmethyl)thio}azetidin-2-one 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 2-oxo-N-[(1R)-1-phenylethyl]-4-(2-pyridylmethylsulfanyl)azetidine-1-carboxamide
  参考文献：
  名称：

  Inhibition of human cytomegalovirus protease N o with monocyclic β-lactams

  摘要：

  Monocyclic beta-lactams have been identified as potent and selective inhibitors of the human cytomegalovirus protease (HCMV) N-o. Two series of these inhibitors are described, a peptidyl series of compounds and non-peptidic molecules featuring lower molecular weights. The SAR work that lead to the discovery of these inhibitors, together with their synthesis is also disclosed. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00240-6
• 作为产物：
  描述：

  thioacetic acid S-pyridin-2-ylmethyl ester 在 sodium hydroxide 、 三乙胺 、 palladium dichloride 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 4-{(2-pyridinylmethyl)thio}azetidin-2-one
  参考文献：
  名称：

  Inhibition of human cytomegalovirus protease N o with monocyclic β-lactams

  摘要：

  Monocyclic beta-lactams have been identified as potent and selective inhibitors of the human cytomegalovirus protease (HCMV) N-o. Two series of these inhibitors are described, a peptidyl series of compounds and non-peptidic molecules featuring lower molecular weights. The SAR work that lead to the discovery of these inhibitors, together with their synthesis is also disclosed. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00240-6

文献信息

• Azetidinone derivatives for the treatment of HCMV infections
  申请人：Boehringer Ingelheim (Canada) Ltd.

  公开号：US06239125B1

  公开（公告）日：2001-05-29

  A compound of formula 1: wherein Y is S or O; R1 is C1-6 alkyl; (C0-6 alkyl)aryl; (C0-6 alkyl)Het; or R1 is an amino acid analog or dipeptide analog of the formula: wherein R2 is H, C1-10 alkyl; or an amide or ester group; A is C6-10 aryl, Het or CH—R3 wherein R3 is C1-6 alkyl or (C0-4 alkyl)aryl; and Z is H, C1-6 alkyl, or an acyl; R4 is hydrogen, lower alkyl, methoxy, ethoxy, or benzyloxy; and R5 is alkyl, cycloalkyl, carboxyl group; an aryl; Het or Het(lower alkyl); or R4 and R5 together with the nitrogen atom to which they are attached form a nitrogen containing ring optionally substituted with phenyl or C(O)OCH2-phenyl, said phenyl ring optionally mono- or di-substituted with among others C(O)OR7 wherein R7 is lower alkyl or phenyl(lower alkyl); or a therapeutically acceptable acid addition salt thereof which compounds are useful in the treatment of HCMV infections.

  化合物的化学式为1：其中Y为S或O；R1为C1-6烷基；(C0-6烷基)芳基；(C0-6烷基)杂环基；或R1为氨基酸类似物或二肽类似物的化学式：其中R2为H，C1-10烷基；或酰胺或酯基；A为C6-10芳基，杂环基或CH—R3，其中R3为C1-6烷基或(C0-4烷基)芳基；Z为H，C1-6烷基或酰基；R4为氢，低烷基，甲氧基，乙氧基或苄氧基；R5为烷基，环烷基，羧基；芳基；杂环基或杂环基(低烷基)；或R4和R5与它们连接的氮原子一起形成一个含氮环，该环可选择地被苯基或C(O)OCH2-苯基取代，所述苯环可选择地单取代或二取代，其中包括C(O)OR7，其中R7为低烷基或苯基(低烷基)；或其治疗上可接受的酸盐，这些化合物可用于治疗HCMV感染。
• AZETIDINONE DERIVATIVES FOR THE TREATMENT OF HCMV INFECTIONS
  申请人：BOEHRINGER INGELHEIM (CANADA) LTD.

  公开号：EP1021404A1

  公开（公告）日：2000-07-26
• US6239125B1
  申请人：——

  公开号：US6239125B1

  公开（公告）日：2001-05-29
• [EN] AZETIDINONE DERIVATIVES FOR THE TREATMENT OF HCMV INFECTIONS<br/>[FR] DERIVES D'AZETIDINONE POUR LE TRAITEMENT D'INFECTIONS HCMV
  申请人：BOEHRINGER INGELHEIM (CANADA) LTD.

  公开号：WO1999018071A1

  公开（公告）日：1999-04-15

  (EN) A compound of formula (1) wherein Y is S or O; R1 is C1-6 alkyl; (C0-6 alkyl)aryl; (C0-6 alkyl)Het; or R1 is an amino acid analog or dipeptide analog of formula (I) wherein R2 is H, C1-10 alkyl; or an amide or ester group; A is C6-10 aryl, Het or CH-R3 wherein R3 is C1-6 alkyl or (C0-4 alkyl)aryl; and Z is H, C1-6 alkyl, or an acyl; R4 is hydrogen, lower alkyl, methoxy, ethoxy, or benzyloxy; and R5 is alkyl, cycloalkyl, carboxyl group; an aryl; Het or Het(lower alkyl); or R4 and R5 together with the nitrogen atom to which they are attached form a nitrogen containing ring optionally substituted with phenyl or C(O)OCH2-phenyl, said phenyl ring optionally mono- or di-substituted with among others C(O)OR7 wherein R7 is lower alkyl or phenyl (lower alkyl); or a therapeutically acceptable acid addition salt thereof.(FR) L'invention concerne un composé de formule (1) dans laquelle Y désigne S ou O; R1 désigne un alkyle C1-6; (alkyl C0-6)aryle; (alkyl C0-6)Het; ou R1 désigne un analogue d'acide aminé ou analogue dipeptidique de la formule (I) dans laquelle R2 désigne H, alkyle C1-10; ou un groupe amide ou ester; A désigne un aryle C6-10, Het ou CH-R3 où R3 désigne un alkyle C1-6 ou (alkyl C0-4)aryle; et Z désigne H, alkyle C1-6 ou un acyle; R4 désigne l'hydrogène, un alkyle inférieur, méthoxy, éthoxy ou benzyloxy; et R5 désigne un alkyle, cycloalkyle, groupe carboxyle, un aryle; Het ou Het(alkyle inférieur); ou R4 et R5 pris ensemble avec l'atome d'azote auquel ils sont liés forment un cycle contenant de l'azote éventuellement substitué par phényle ou C(O)OCH2-phényle; ledit cycle phényle éventuellement mono- ou di-substitué par entre autres C(O)OR7 où R7 désigne un alkyle inférieur ou phényl(alkyle inférieur); ou un de ses sels d'addition d'acide thérapeutiquement acceptable.