5-[(dimethylamino)methylene]-6,7-dihydro-1-benzothiophen-4(5H)-one | 84670-60-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-[(dimethylamino)methylene]-6,7-dihydro-1-benzothiophen-4(5H)-one
• 英文别名: (E)-5-((Dimethylamino)methylene)-6,7-dihydrobenzo[B]thiophen-4(5H)-one；(5E)-5-(dimethylaminomethylidene)-6,7-dihydro-1-benzothiophen-4-one
• CAS: 84670-60-0
• 化学式: C₁₁H₁₃NOS
• 分子量: 207.296
• InChiKey: NACNWVIODNHIQA-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  48.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-[(dimethylamino)methylene]-6,7-dihydro-1-benzothiophen-4(5H)-one 在 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 反应 17.0h， 生成 3-氯-4-二甲基氨基硫代异补骨脂素
  参考文献：
  名称：

  Mosti; Schenone; Menozzi, Farmaco, Edizione Scientifica, 1984, vol. 39, # 2, p. 81 - 94

  摘要：

  DOI：
• 作为产物：
  描述：

  (5E)-5-(hydroxymethylidene)-6,7-dihydro-1-benzothiophen-4-one 、 二甲胺 以95%的产率得到
  参考文献：
  名称：

  MOSTI L.;SCHENONE P.;MENOZZI G.;ROMUSSI G., J. HETEROCYCL. CHEM., 1982, 19, NO 5, 1057-1059

  摘要：

  DOI：

文献信息

• Compositions useful as inhibitors of protein kinases
  申请人：Jimenez Juan-Miguel

  公开号：US20050148603A1

  公开（公告）日：2005-07-07

  The present invention relates to compounds useful as inhibitors of protein kinases. The invention also provides processes for preparing the compounds, pharmaceutically acceptable compositions comprising the compounds, and methods of using the compounds and compositions in the treatment of various disease, conditions, or disorders.

  本发明涉及作为蛋白激酶抑制剂有用的化合物。该发明还提供了制备这些化合物的方法，包括这些化合物的药用可接受组合物，以及在治疗各种疾病、症状或障碍中使用这些化合物和组合物的方法。
• [EN] FUSED POLYCYCLIC 2-AMINOPYRIMIDINE DERIVATIVES, THEIR PREPARATION AND THEIR USE AS PROTEIN TYROSINE KINASE INHIBITORS<br/>[FR] DERIVES POLYCYCLIQUE FONDUS DE 2-AMINOPYRIMIDINE, LEUR PREPARATION ET LEUR UTILISATION COMME INHIBITEURS DE PROTEINE TYROSINE-KINASE
  申请人：CELLTECH THERAPEUTICS LIMITED

  公开号：WO1998028281A1

  公开（公告）日：1998-07-02

  (EN) Fused polycyclic 2-aminopyrimidines of formula (1) wherein Ar is an optionally substituted aromatic or heteroaromatic group; X is a carbon or nitrogen atom; Y is a carbon or nitrogen atom; Z is a linker group; A together with X and Y forms an optionally substituted monocyclic or bicyclic aromatic or heteroaromatic group; and the salts, solvates, hydrates and N-oxides thereof are described. The compounds are potent and selective inhibitors of the protein tyrosine kinases p56lck and p59fyn and are of use in the prophylaxis and treatment of immune diseases, hyperproliferative disorders and other diseases in which inappropriate p56lck and/or p59fyn activity is believed to have a role.(FR) L'invention concerne des 2-aminopyrimidine polycycliques fondus, ainsi que leurs sels, solvates, hydrates et N-oxydes, et représentés par la formule (1), dans laquelle Ar est un groupe aromatique ou hétéro-aromatique éventuellement substitué; X est atome de carbone ou d'azote; Y est atome de carbone ou d'azote; Z est un groupe lieur; A, X et Y forment un groupe aromatique ou hétéro-aromatique, monocyclique ou bicyclique, éventuellement substitué. Ces composés, qui sont des inhibiteurs puissants et sélectifs des protéines tyrosines kinases p561ck et p59fyn, conviennent particulièrement à la prophylaxie et au traitement de maladies immunitaires, de maladies hyperproliférantes et d'autres maladies dans lesquelles on pense qu'une activité inappropriée de la p561ck et/ou p59fyn joue un rôle.

  (中) 本发明涉及一种融合多环的2-氨基嘧啶化合物，其化学式为（1），其中Ar为可选取代的芳香族或杂芳族基；X为碳或氮原子；Y为碳或氮原子；Z为连接基；A与X和Y一起形成一个可选取代的单环或双环芳香族或杂芳族基；以及它们的盐、溶剂化物、水合物和N-氧化物。这些化合物是蛋白酪氨酸激酶p56lck和p59fyn的有效且选择性的抑制剂，并可用于预防和治疗免疫性疾病、增生性疾病和其他疾病，在这些疾病中，p56lck和/或p59fyn的不适当活性被认为发挥了作用。
• COMPOSITIONS USEFUL AS INHIBITORS OF PROTEIN KINASES
  申请人：Jimenez Juan-Miguel

  公开号：US20100280026A1

  公开（公告）日：2010-11-04

  The present invention relates to compounds useful as inhibitors of protein kinases. The invention also provides processes for preparing the compounds, pharmaceutically acceptable compositions comprising the compounds, and methods of using the compounds and compositions in the treatment of various disease, conditions, or disorders.

  本发明涉及作为蛋白激酶抑制剂有用的化合物。该发明还提供了制备这些化合物的方法，包括这些化合物的药学上可接受的组合物，以及使用这些化合物和组合物治疗各种疾病、状况或障碍的方法。
• Defining the structure-activity relationship for a novel class of allosteric MKP5 inhibitors
  作者：Zachary T.K. Gannam、Haya Jamali、Oh Sang Kweon、James Herrington、Shanelle R. Shillingford、Christina Papini、Erik Gentzel、Elias Lolis、Anton M. Bennett、Jonathan A. Ellman、Karen S. Anderson

  DOI：10.1016/j.ejmech.2022.114712

  日期：2022.12

  Mitogen-activated protein kinase (MAPK) phosphatase 5 (MKP5) is responsible for regulating the activity of the stress-responsive MAPKs and has been put forth as a potential therapeutic target for a number of diseases, including dystrophic muscle disease a fatal rare disease which has neither a treatment nor cure. In previous work, we identified Compound 1 (3,3-dimethyl-1-((9-(methylthio)-5,6-dihydrothieno[3

  丝裂原激活蛋白激酶 (MAPK) 磷酸酶 5 (MKP5) 负责调节应激反应性 MAPK 的活性，并已被提出作为许多疾病的潜在治疗靶点，包括营养不良性肌肉病，这是一种致命的罕见疾病，既没有治疗方法也没有治愈方法。在之前的工作中，我们鉴定了化合物1 (3,3-二甲基-1-((9-(甲硫基)-5,6-二氢噻吩并[3,4 -h ]喹唑啉-2-基)硫基)丁-2-酮）作为一类新型 MKP5 抑制剂的先导化合物。在这项工作中，我们通过对1中存在的支架和官能团的修饰来探索抑制 MKP5 的结构-活性关系。设计、合成并评估了一系列衍生化合物对 MKP5 的抑制作用。此外，还解析了六种酶-抑制剂复合物的X射线晶体结构，进一步阐明了MKP5抑制的必要条件。我们发现抑制剂三环核心和 Tyr435 之间的平行位移 π-π 相互作用对于调节效力至关重要，并且对核心的修饰和 C-9 位点的功能化对于确保核心的正确定位
• Novel angular furo and thieno-quinolinones: synthesis and preliminary photobiological studies
  作者：Paola Fossa、Luisa Mosti、Giulia Menozzi、Cristina Marzano、Franca Baccichetti、Franco Bordin

  DOI：10.1016/s0968-0896(01)00328-5

  日期：2002.3

  A number of new furo and thienoquinolinones carrying an electron-withdrawing function or unsubstituted at the position 3 were synthesized in order to obtain new potential photochemotherapeutic agents with increased anti proliferative activity and decreased toxic side effects. Our interest in studying the SAR of these derivatives also prompted us to investigate the influence of N-methylation on biological activity, by preparing N-methyl derivatives. The antiproliferative activity of all the newly synthesized compounds was evaluated and compared to 8-methoxypsoralen (8-MOP), the drug widely used in PUVA-therapy. The 3-unsubstituted thienoquinolinones were generally the most potent derivatives, followed by the furo-analogues. In particular. the unsubstituted thieno[2.3-h]quinoline-2(1H)one showed the highest activity in T2 bacteriophage, HeLa cells and Ehrlich cells tests. All the compounds, assayed on Escherichia coli WP2 TM9, showed a similar mutagenic activity, very close to that of 8-MOP. Except for 2-oxo-1,2-dihydrothieno[2.3-h]quinoline-3-carboxylic acid, which appeared to be very effective, all compounds generated singlet oxygen to slightly larger amounts when compared to 8-MOP. The N-methyl analogues only induced moderate skin erythemas on albino guinea pigs, while all other derivatives appeared to be entirely inactive. On the basis of these results, the unsubstituted thieno[2,3h]quinoline 2(1H)one seems to be the most interesting potential drug for PUVA photochemotherapy and photopheresis. (C) 2002 Elsevier Science Ltd. All rights reserved.