tert-butyl 3-(benzo[d]thiazol-2-yl)azetidine-1-carboxylate | 1180653-89-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: tert-butyl 3-(benzo[d]thiazol-2-yl)azetidine-1-carboxylate
• 英文别名: 3-benzothiazol-2-yl-azetidine-1-carboxylic acid tert-butyl ester；tert-butyl 3-(1,3-benzothiazol-2-yl)azetidine-1-carboxylate
• CAS: 1180653-89-7
• 化学式: C₁₅H₁₈N₂O₂S
• 分子量: 290.386
• InChiKey: DSTGRFYSANLVJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  70.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl 3-(benzo[d]thiazol-2-yl)azetidine-1-carboxylate 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 (E)-6-(3-(3-(benzo[d]thiazol-2-yl)azetidin-1-yl)-3-oxoprop-1-en-1-yl)-3,4-dihydro-1,8-naphthyridin-2(1H)-one
  参考文献：
  名称：

  Discovery of azetidine based ene-amides as potent bacterial enoyl ACP reductase (FabI) inhibitors

  摘要：

  A novel and potent series of ene-amides featuring azetidines has been developed as FabI inhibitors active against drug resistant Gram-positive pathogens particularly staphylococcal organisms. Most of the compounds from the series possessed excellent biochemical inhibition of Staphylococcus aureus FabI enzyme and whole cell activity against clinically relevant MRSA, MSSA and MRSE organisms which are responsible for significant morbidity and mortality in community as well as hospital settings. The binding mode of one of the leads, AEA16, in Escherichia coli FabI enzyme was determined unambiguously using X-ray crystallography. The lead compounds displayed good metabolic stability in mice liver microsomes and pharmacokinetic profile in mice. The in vivo efficacy of lead AEA16 has been demonstrated in a lethal murine systemic infection model.

  DOI：

  10.1016/j.ejmech.2014.07.036
• 作为产物：
  描述：

  苯并噻唑 、 1-Boc-3-碘氮杂环丁烷 在 dipotassium peroxodisulfate 、 N,N-二异丙基乙胺 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 2.0h， 以45%的产率得到tert-butyl 3-(benzo[d]thiazol-2-yl)azetidine-1-carboxylate
  参考文献：
  名称：

  氨基烷基自由基作为卤原子转移剂，用于活化烷基和芳基卤化物

  摘要：

  胺作为通往烷基自由基的途径 近年来，由蓝光驱动的光氧化还原催化经常被用于氧化与氮相邻的碳中心。康斯坦丁等人。现在表明，这些氨基烷基可以反过来方便地从各种烷基碳上剥离碘原子。产生的新烷基很容易进行氘化和偶联，例如烷基化、烯丙基化和烯化。结果是简单的胺可以在卤代烃的均裂活化和功能化中替代更危险的常规试剂，例如三烷基锡化合物。科学，这个问题 p。1021 被光活化染料方便地氧化的胺可以裂解碳-碘键以产生烷基。有机卤化物是合成中的重要组成部分，但它们在（光）氧化还原化学中的应用受到其低还原电位的限制。尽管需要危险的试剂和引发剂（如氢化三丁基锡），但卤素原子转移仍然是在自由基过程中利用这些底物的最可靠方法。在这项研究中，我们证明了容易从简单胺中获得的 α-氨基烷基自由基促进了碳 - 卤素键的均裂活化，其反应性曲线反映了经典锡自由基的反应性。这种策略可以方便地将烷基和芳基卤化物参与广泛的氧化还原转化，以在温和的条件下以高化学选择性构建

  DOI：

  10.1126/science.aba2419

文献信息

• [EN] 6,7,8,9-TETRAHYDRO-5H-1,4,7,10A-TETRAAZA-CYCLOHEPT[F]INDENE DERIVATIVES, PHARMACEUTICAL COMPOSITIONS CONTAINING THESE COMPOUNDS, THEIR USE AND PROCESSES FOR PREPARING THEM<br/>[FR] DÉRIVÉS DE 6,7,8,9-TÉTRAHYDRO-5H-1,4,7,10A-TÉTRAAZA-CYCLOHEPT[F]INDÈNE, COMPOSITIONS PHARMACEUTIQUES CONTENANT CES COMPOSÉS, LEUR UTILISATION ET PROCÉDÉS POUR PRÉPARER CEUX-CI
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2010060952A1

  公开（公告）日：2010-06-03

  The present invention relates to compounds defined by formula (I), wherein the groups X, Y, W and R1 to R4 are defined as in claim 1, possessing valuable pharmacological activity. Particularly the compounds are agonists of the 5-HT2C receptor, and thus are suitable for treatment and prevention of diseases which can be influenced by inhibition of this receptor, such as metabolic and CNS-related disorders.

  本发明涉及由式（I）定义的化合物，其中基团X、Y、W和R1至R4如权利要求1中所定义，具有有价值的药理活性。特别是这些化合物是5-HT2C受体的激动剂，因此适用于治疗和预防可以受到该受体抑制影响的疾病，如代谢和中枢神经系统相关疾病。
• 6,7,8,9-Tetrahydro-5H-1,4,7,10a-tetraaza-cyclohept[f]indene derivatives, pharmaceutical compositions containing these compounds, their use and processes for preparing them
  申请人：Mueller Stephan-Georg

  公开号：US20120165304A1

  公开（公告）日：2012-06-28

  The present invention relates to compounds defined by formula (I), wherein the groups X, Y, W and R 1 to R 4 are defined as in claim 1 , possessing valuable pharmacological activity. Particularly the compounds are agonists of the 5-HT2C receptor, and thus are suitable for treatment and prevention of diseases which can be influenced by inhibition of this receptor, such as metabolic and CNS-related disorders.

  本发明涉及由式(I)定义的化合物，其中X、Y、W和R1至R4基团如权利要求1中所定义，具有有价值的药理活性。特别地，这些化合物是5-HT2C受体激动剂，因此适用于治疗和预防可以受到该受体抑制影响的疾病，例如代谢和中枢神经系统相关疾病。
• 6,7,8,9-tetrahydro-5H-1,4,7,10a-tetraaza-cyclohept[f]indene derivatives, pharmaceutical compositions containing these compounds, their use and processes for preparing them
  申请人：Mueller Stephan-Georg

  公开号：US09346816B2

  公开（公告）日：2016-05-24

  The present invention relates to compounds defined by formula I wherein the groups X, Y, W and R1 to R4 are defined as in claim 1, possessing valuable pharmacological activity. Particularly the compounds are agonists of the 5-HT2C receptor, and thus are suitable for treatment and prevention of diseases which can be influenced by inhibition of this receptor, such as metabolic and CNS-related disorders.

  本发明涉及一种由式I定义的化合物，其中X、Y、W和R1至R4基团如权利要求1所定义，具有有价值的药理活性。特别地，这些化合物是5-HT2C受体激动剂，因此适用于治疗和预防可以通过抑制该受体受影响的代谢和中枢神经系统相关疾病。
• Redefining the Synthetic Logic of Medicinal Chemistry. Photoredox-Catalyzed Reactions as a General Tool for Aliphatic Core Functionalization
  作者：David F. Fernández、María González-Esguevillas、Sebastian Keess、Felix Schäfer、Jens Mohr、Andre Shavnya、Thomas Knauber、David C. Blakemore、David W. C. MacMillan

  DOI：10.1021/acs.orglett.3c00994

  日期：2024.4.12

  C(sp3)-rich aliphatic motifs in drug molecules are strongly associated with clinical success. Historically, the availability of compound libraries based on C(sp3)-rich cores has been limited due to the challenging direct functionalization of aliphatic rings. Instead, most small molecule drug-like libraries are diversified around central aromatic rings. Herein, we present a general approach to the synthesis

  药物分子中富含 C(sp 3 ) 的脂肪族基序与临床成功密切相关。从历史上看，由于脂肪环的直接功能化具有挑战性，基于富含 C(sp 3 ) 核心的化合物库的可用性受到限制。相反，大多数小分子类药物库围绕中心芳香环进行多样化。在此，我们提出了一种在温和条件下通过光氧化还原催化合成具有脂肪族核心环的多样化文库的通用方法。
• Preparation of Heteroaryloxetanes and Heteroarylazetidines by Use of a Minisci Reaction
  作者：Matthew A. J. Duncton、M. Angels Estiarte、Russell J. Johnson、Matthew Cox、Donogh J. R. O’Mahony、William T. Edwards、Michael G. Kelly

  DOI：10.1021/jo9010624

  日期：2009.8.21

  Introduction of oxetan-3-yl and azetidin-3-yl groups into heteroaromatic bases was achieved by using a radical addition method (Minisci reaction). To demonstrate utility. the process was used to introduce an oxetane Or azetidine into heteroaromatic systems that have found important uses in the drug discovery industry, such as the marketed EGFR inhibitor geftinib, a quinolinecarbonitrile Src tyrosine kinase inhibitor, and the antimalarial hydroquinine.