N-(5-溴-2-吡啶基)-2-氯乙酰胺 | 141454-61-7

• 物质功能分类: 医药中间体 - 吡啶类化合物
• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: N-(5-溴-2-吡啶基)-2-氯乙酰胺
• 中文别名: N-[1-(5-溴吡啶-2-基)乙烯基]乙酰胺；N-(5-溴-2-嘧啶基)-2-氯乙酰胺；N-(5-溴吡啶-2-基)-2-氯乙酰胺
• 英文名称: 2-chloro-N-(2-(5-bromo)pyridinyl)acetamide
• 英文别名: N-(5-bromopyridin-2-yl)-2-chloroacetamide；PCM-0102227；N-(5-bromo-2-pyridinyl)-2-chloroacetamide
• CAS: 141454-61-7
• 化学式: C₇H₆BrClN₂O
• mdl: MFCD00461174
• 分子量: 249.494
• InChiKey: OVIDBGFJVRQUPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  N-(5-溴-2-吡啶基)-2-氯乙酰胺 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 9.08h， 生成 C₁₅H₁₃BrClN₃O₂S
  参考文献：
  名称：

  Novel small molecules as apoptosis inducers: Synthesis, preliminary structure–activity relationships, and in vitro biological evaluation

  摘要：

  Inducing apoptosis is a promising therapeutic approach to overcome cancer. In this study, 30 compounds were synthesized and evaluated for their antiproliferative activity against three tumor cell lines in vitro: A875, H460 and Hela cancer cells by the MTT assay. The most potent analogue 7a, a novel compound was first reported by our group, inhibited the proliferation of A875 cells with an IC50 value of 98 nM. Flow cytometry analysis and morphological analysis suggested that compound 7a had potential anticancer efficacy via G(2)/M cell cycle arrest, which could be attributed to its proliferation and apoptosis, and also in a concentration-dependent manner. The SAR analysis indicated that the substituents R-2 played a crucial role in the antiproliferation activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.076
• 作为产物：
  描述：

  2-氨基-5-溴吡啶 、 氯乙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 以81%的产率得到N-(5-溴-2-吡啶基)-2-氯乙酰胺
  参考文献：
  名称：

  合成WAY-100635的[6-吡啶基-18F]标记的氟衍生物，作为PET进行脑5-HT1A受体成像的候选放射性配体。

  摘要：

  近年来，人们在设计，合成和药理表征5-HT（1A）受体拮抗剂WAY-100635的放射性氟化衍生物上进行了大量工作，以利用PET在人脑中体内研究这些受体。合成了WAY-100635的（吡啶基-6）-氟和（吡啶基-5）-氟类似物（6-氟和5-氟WAY-100635，5a / 6a）以及相应的氯，溴-和硝基衍生物作为标记的前体（5b-d和6b-d）。这些前体与氟18的比较放射性标记（发射正电子的同位素，半衰期为109.8分钟）清楚地表明，只有这种吡啶系列中的邻位氟化而不是间位氟化对通过亲核试剂制备放射性配体感兴趣杂芳族取代。6-[（（18F）] Fluoro-WAY-100635（[（18F）] 5a）可以一步有效地从相应的6-溴前体中合成（使用常规方法在145摄氏度下加热10分钟）或来自相应的6-硝基前体（使用100 W微波活化1分钟）。通常，使用15-25 mCi（0.55-0.92 GBq）的6-[（（18）F]

  DOI：

  10.1016/s0968-0896(03)00225-6

文献信息

• Synthesis and biological evaluation of N-(substituted phenyl)-2-(5H-[1,2,4]triazino[5,6-b]indol-3-ylsulfanyl)acetamides as antimicrobial, antidepressant, and anticonvulsant agents
  作者：N. Shruthi、Boja Poojary、Vasantha Kumar、A. Prathibha、Mumtaz Mohammed Hussain、B. C. Revanasiddappa、Himanshu Joshi

  DOI：10.1134/s1068162015020144

  日期：2015.3

  N-Aryl-2-(5H-[1,2,4]triazino[5,6-b]indol-3-ylsulfanyl)acetamides were synthesized by condensation of tricyclic compound 2,5-dihydro-3H-[1,2,4]triazino[5,6-b]indole-3-thione with chloro N-phenylacetamides. The tricyclic compound was obtained by condensation of Isatin with thiosemicarbazide. Chloro N-phenylacetamides were obtained from different substituted anilines. Their structures were characterized by

  通过三环化合物2,5-二氢-3H-缩合合成了一系列新的N-Aryl-2-(5H-[1,2,4]triazino[5,6-b]indol-3-ylsulfanyl)乙酰胺[1,2,4]triazino[5,6-b]indole-3-thione 与氯 N-苯基乙酰胺。三环化合物是由靛红与氨基硫脲缩合得到的。氯 N-苯基乙酰胺是从不同的取代苯胺中获得的。它们的结构通过IR、1H NMR、LC-MS和元素分析表征。筛选新合成的化合物的抗微生物、抗抑郁和抗惊厥活性。初步结果表明，当测试抗微生物活性时，大多数化合物的 MIC 值低于使用的标准药物。一些化合物具有非常好的抗抑郁和抗惊厥活性。
• Design, synthesis, and pharmacological studies of some new Mannich bases and S-alkylated analogs of pyrazole integrated 1,3,4-oxadiazole
  作者：Shivapura Viveka、Dinesha、Prasanna Shama、Gundibasappa Karikannar Nagaraja、Nagaraju Deepa、Marikunte Yanjarappa Sreenivasa

  DOI：10.1007/s11164-015-2170-7

  日期：2016.3

  A facile and convenient synthesis of Mannich bases 5a – f and S -alkylated derivatives 6a – f and 7a – f has been carried out from the key intermediate 5-(5-methyl-1-phenyl-1 H -pyrazol-4-yl)-1,3,4-oxadiazole-2(3 H )-thione ( 4 ). Intermediate 4 was obtained from one-pot reaction of ethyl acetoacetate, phenylhydrazine, and N , N -dimethylformamide dimethyl acetal (DMF-DMA) followed by reaction with

  从关键中间体5-（5-甲基-1-苯基-1 H- 吡唑-4-基）进行了 曼尼希碱 5a - f 和 S- 烷基化衍生物 6a - f 和 7a - f的 简便合成 ）-1,3,4-恶二唑-2（3 H ）-硫酮（ 4 ）。中间体 4 是从一锅乙酰乙酸乙酯，苯肼和 N ， N的 反应中获得的 -二甲基甲酰胺二甲基乙缩醛（DMF-DMA），然后与水合肼和二硫化碳反应。根据元素分析，红外（IR），1 H核磁共振（NMR），13 C NMR和质谱数据建立了新合成化合物的结构。筛选所有合成的化合物的体内抗炎，体内止痛和体外抗微生物活性。从活性研究中可以得出结论，在所有衍生物中，化合物 5c ， 5e ， 5f ， 6c ， 7b 和 7c 显示出有效的抗炎活性，而 5b ， 图5c ， 图5e ， 图5f ， 6C ， 6F ， 图7b ， 图7c 和 7e中 显示出良好的镇痛活性。化合物 6a ， 6c
• Synthesis and Biological Evaluation of Novel Benzothiazole-2-thiol Derivatives as Potential Anticancer Agents
  作者：Xuan-Hong Shi、Zhao Wang、Yong Xia、Ting-Hong Ye、Mei Deng、You-Zhi Xu、Yu-Quan Wei、Luo-Ting Yu

  DOI：10.3390/molecules17043933

  日期：——

  A series of novel benzothiazole-2-thiol derivatives were synthesized and their structures determined by 1H-NMR, 13C-NMR and HRMS (ESI). The effects of all compounds on a panel of different types of human cancer cell lines were investigated. Among them, pyridinyl-2-amine linked benzothiazole-2-thiol compounds 7d, 7e, 7f and 7i exhibited potent and broad-spectrum inhibitory activities. Compound 7e displayed the most potent anticancer activity on SKRB-3 (IC50 = 1.2 nM), SW620 (IC50 = 4.3 nM), A549 (IC50 = 44 nM) and HepG2 (IC50 = 48 nM) and was found to induce apoptosis in HepG2 cancer cells.

  研究人员合成了一系列新型苯并噻唑-2-硫醇衍生物，并通过 1H-NMR、13C-NMR 和 HRMS (ESI) 确定了它们的结构。研究了所有化合物对不同类型人类癌细胞株的影响。其中，与苯并噻唑-2-硫醇相连的吡啶基-2-胺化合物 7d、7e、7f 和 7i 具有强效、广谱的抑制活性。化合物 7e 对 SKRB-3（IC50 = 1.2 nM）、SW620（IC50 = 4.3 nM）、A549（IC50 = 44 nM）和 HepG2（IC50 = 48 nM）的抗癌活性最强，并能诱导 HepG2 癌细胞凋亡。
• [EN] OXAZOLE AND THIOAZOLE-TYPE CULLIN RING UBIQUITIN LIGASE COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS D'UBIQUITINE LIGASE CULLIN RING DU TYPE THIOAZOLE ET OXAZOLE ET LEURS UTILISATIONS
  申请人：CEMM FORSCHUNGSZENTRUM FUER MOLEKULARE MEDIZIN GMBH

  公开号：WO2021074414A1

  公开（公告）日：2021-04-22

  The present invention relates to compounds with the ability to stimulate/induce ubiquitination of a target protein/target proteins. The compounds of the present invention may stimulate/induce ubiquitination of a target protein/target proteins; i.e. via degradation of a target protein/target proteins by the cullin-RING ubiquitin ligase (CRL). Such target protein/target proteins may be proteins involved in diseases, like cancer, metabolic disorder, infectious disease and/or neurological disorder. The invention further relates to a method for identifying/obtaining and/or testing a compound able to induce ubiquitination of a target protein/target proteins. The invention also relates to the compounds and composition for use as medicaments as well as pharmaceutical compositions comprising these compounds. Particularly, the compounds of the present invention may degrade proteins associated with cancer, metabolic disorder, infectious disease and/or neurological disorder. Furthermore, the present invention relates the compounds for use as a medicament, such as for use in treating cancer, metabolic disorder, infectious disease and/or neurological disorder and to a method for treating a disease, such as cancer, metabolic disorder, infectious disease and/or neurological disorder, comprising administering the compound of the present invention.

  本发明涉及具有刺激/诱导靶蛋白泛素化能力的化合物。本发明的化合物可能通过cullin-RING泛素连接酶（CRL）降解靶蛋白，从而刺激/诱导靶蛋白的泛素化；这些靶蛋白可能是与疾病（如癌症、代谢紊乱、传染病和/或神经疾病）有关的蛋白质。该发明还涉及一种用于识别/获取和/或测试能够诱导靶蛋白泛素化的化合物的方法。该发明还涉及用作药物的化合物和组合物，以及包含这些化合物的药物组合物。特别是，本发明的化合物可能降解与癌症、代谢紊乱、传染病和/或神经疾病相关的蛋白质。此外，本发明涉及用作药物的化合物，例如用于治疗癌症、代谢紊乱、传染病和/或神经疾病，并且涉及一种治疗疾病的方法，如癌症、代谢紊乱、传染病和/或神经疾病，包括给予本发明的化合物。
• [EN] METHODS AND COMPOSITIONS FOR THE TREATMENT OF INFLUENZA<br/>[FR] MÉTHODES ET COMPOSITIONS POUR LE TRAITEMENT DE LA GRIPPE
  申请人：UNIV TEXAS

  公开号：WO2021189080A1

  公开（公告）日：2021-09-23

  The present disclosure provides, in part, compositions, kits and methods for treating or preventing an influenza viral infection by administering a therapeutically effective amount of an inhibitor of influenza viral M mRNA nuclear export to a subject in need.

  本公开说明部分提供了治疗或预防流感病毒感染的组合物、试剂盒和方法，通过向需要的受体内投与流感病毒M mRNA核出口抑制剂的治疗有效量来实现。