6-bromo-indoline-2,3-dione-3-oxime | 115049-55-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 6-bromo-indoline-2,3-dione-3-oxime
• 英文别名: 6-Bromisatin-β-oxim；6-Brom-indolin-2,3-dion-3-oxim
• CAS: 115049-55-3
• 化学式: C₈H₅BrN₂O₂
• 分子量: 241.044
• InChiKey: FSSUCRFOBNKBNP-UHFFFAOYSA-N

物化性质

• 密度：
  1.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.58
• 重原子数：
  13.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.69
• 氢给体数：
  2.0
• 氢受体数：
  3.0

文献信息

• Synthesis and Dual D<sub>2</sub> and 5-HT<sub>1A</sub> Receptor Binding Affinities of 7-piperazinyl and 7-piperidinyl-3,4-dihydroquinazolin-2(1H)-ones
  作者：Nisar Ullah

  DOI：10.2174/15734064113096660046

  日期：2014.5.31

  A series of new 7-piperazinyl and 7-piperidinyl-3,4-dihydroquinazolin-2(1H)-ones has been synthesized. The described compounds are structurally related to adoprazine, a potential atypical antipsychotic bearing potent D2 receptor antagonist and 5-HT1A receptor agonist properties. Suitably modified aryl bromides were prepared and condensed with tert-butyl piperazine-1-carboxylate to afford the advanced intermediate piperazinyl-3,4-dihydroquinazolin-2(1H)-one. Likewise Suzuki-Miyaura cross-coupling reaction of cyclic vinyl boronate with appropriate aryl bromides rendered piperidinyl-3,4-dihydroquinazolin-2(1H)-one. The reductive amination of the piperazinyl and piperidinyl-3,4- dihydroquinazolin-2(1H)-ones with suitably designed biarylaldehydes accomplished the synthesis of these title compounds. The described compounds were screened for D2 and 5-HT1A receptors binding affinities. The structure-activity relationship studies revealed that cyclopentenylpyridine and cyclopentenylbenzyl groups contribute significantly to the dual D2 and 5-HT1A receptor binding affinities of these compounds.

  一系列新的7-哌嗪基和7-哌啶基-3,4-二氢喹唑啉-2(1H)-酮已被合成。所述化合物在结构上与阿多拉嗪相关，后者是一种潜在的不典型抗精神病药物，具有强效的D2受体拮抗剂和5-HT1A受体激动剂特性。制备了适当修饰的芳基溴化物，并与叔丁基哌嗪-1-羧酸酯缩合，得到高级中间体哌嗪基-3,4-二氢喹唑啉-2(1H)-酮。同样，Suzuki-Miyaura交叉偶联反应中，环状乙烯基硼酸盐与适当的芳基溴化物反应，得到哌啶基-3,4-二氢喹唑啉-2(1H)-酮。通过哌嗪基和哌啶基-3,4-二氢喹唑啉-2(1H)-酮与适当设计的联芳基醛的还原胺化反应，完成了这些目标化合物的合成。所述化合物被筛选为D2和5-HT1A受体结合亲和力。结构-活性关系研究表明，环戊烯基吡啶和环戊烯基苄基对这些化合物的双重D2和5-HT1A受体结合亲和力有显著贡献。
• Copper-Catalyzed Carbonyl Group Controlled Coupling of Isatin Oximes with Arylboronic Acids To Prepare <i>N</i> -Aryloxindole Nitrones
  作者：Xue-Ling Mo、Chun-Hua Chen、Cui Liang、Dong-Liang Mo

  DOI：10.1002/ejoc.201701324

  日期：2018.1.17

  prepared in good to excellent yields by copper-catalyzed coupling of N-unprotected isatin oximes with aryl boronic acids under mild reaction conditions. The reaction was tolerant various arylboronic acids with diverse sensitive functional groups. Detailed studies showed that the carbonyl group in isatin oximes might be served as a carbonyl ligand or a controlled group playing important roles in the formation

  在温和的反应条件下，通过 N-未保护的靛红肟与芳基硼酸的铜催化偶联，制备了多种 (E)-N-芳基羟吲哚硝酮，收率良好至极好。该反应耐受具有多种敏感官能团的各种芳基硼酸。详细研究表明，靛红肟中的羰基可能作为羰基配体或受控基团在（E）羟吲哚硝酮的形成中起重要作用。这种用于制备 (E)-N-芳基羟吲哚硝酮的方法很容易在克级规模下进行，并且可以有效地以高产率合成雌酮衍生的羟吲哚硝酮。
• Dihydroquinone derivatives of piperidine and piperazine
  申请人：King Fahd University of Petroleum and Minerals

  公开号：US08916704B1

  公开（公告）日：2014-12-23

  The dihydroquinone derivatives of piperidine and piperazine are 7-piperazinyl and 7-piperadinyl-3,4-dihydroquinazolin-2(1H)-ones that exhibit D2 and 5-HT1A receptor binding affinities, making them suitable for use as the active ingredient of pharmaceuticals for the treatment of schizophrenia. The derivatives have the general formula: where X is carbon or nitrogen and R is a group selected from a through f having the formula: or a pharmaceutically acceptable salt thereof. The piperazine compounds are prepared by condensing 4-bromo-2-nitro-benzonitrile with 1-Boc-piperazine (1-tert-butoxycarbonyl-piperazine) to form an intermediate that is converted to a piperazinyl-3,4-dihydroquinazolin-2(1H)-one. Subsequent reductive amination with the biarylaldehydes a through f completes the synthesis of the 7-piperazinyl-3,4-dihydroquinazolin-2(1H)-ones. The piperadinyl compounds are prepared from tert-butyl-4-(2-oxo-1,2,3,4-tetradihydroquinazolin-7-yl)piperidine-1-carboxylate, which is converted to 7-(piperidin-4-yl)-3,4-dihyroquinazolin-2(1H)-one. Subsequent reductive amination with the biarylaldehydes a through f completes the synthesis of the 7-piperidinyl-3,4-dihydroquinazolin-2(1H)-ones.

  哌啶和哌嗪的二氢喹啉衍生物是7-哌嗪基和7-哌啶基-3,4-二氢喹唑啉-2(1H)-酮，具有D2和5-HT1A受体结合亲和力，使它们适合用作治疗精神分裂症的药物的活性成分。这些衍生物具有一般公式：其中X是碳或氮，R是从a到f的具有以下结构的基团：或其药用可接受的盐。哌嗪化合物通过将4-溴-2-硝基苯腈与1-Boc-哌嗪(1-叔丁氧羰基-哌嗪)缩合制备，形成一个中间体，该中间体转化为哌嗪基-3,4-二氢喹唑啉-2(1H)-酮。随后与二芳基醛a至f进行还原胺化反应，完成了7-哌嗪基-3,4-二氢喹唑啉-2(1H)-酮的合成。哌啶化合物是从叔丁基-4-(2-氧代-1,2,3,4-四氢喹唑啉-7-基)哌啶-1-羧酸酯制备的，将其转化为7-(哌啶-4-基)-3,4-二羟喹唑啉-2(1H)-酮。随后与二芳基醛a至f进行还原胺化反应，完成了7-哌啶基-3,4-二氢喹唑啉-2(1H)-酮的合成。
• Copper-Catalyzed Selective <i>N</i>-Vinylation of 3-(Hydroxyimino)indolin-2-ones with Alkenyl Boronic Acids: Synthesis of <i>N</i>-Vinyl Nitrones and Spirooxindoles
  作者：Chun-Hua Chen、Qing-Qing Liu、Xiao-Pan Ma、Yu Feng、Cui Liang、Cheng-Xue Pan、Gui-Fa Su、Dong-Liang Mo

  DOI：10.1021/acs.joc.7b00620

  日期：2017.6.16

  A copper-catalyzed selective cross-coupling reaction of 3-(hydroxyimino)indolin-2-ones with alkenyl boronic acids to access (E)-N-vinyl oxindole nitrones has been achieved under mild conditions. The studies showed that catalytic copper salt selectively gave mono N-vinylation products, while 2.0 equiv of copper salt provided double N-vinylation products. The control experiments revealed that the carbonyl

  在温和的条件下，铜催化了3-（羟基亚氨基）吲哚啉-2-酮与烯基硼酸的选择性交联反应，以使其进入（E）-N-乙烯基氧吲哚腈。研究表明，催化铜盐选择性生成单N-乙烯基化产物，而2.0当量的铜盐则提供双N-乙烯基化产物。对照实验表明3-（羟基亚氨基）吲哚-2-酮中的羰基对N-乙烯基化起重要作用。此外，在热条件下，可以将制备的N-乙烯基氧吲哚硝酮以良好的产率转化为螺硫辛多。
• DIHYDROQUINONE DERIVATIVES OF PIPERIDINE AND PIPERAZINE
  申请人：KING FAHD UNIVERSITY OF PETROLEUM AND MINERALS

  公开号：US20150094467A1

  公开（公告）日：2015-04-02

  The dihydroquinone derivatives of piperidine and piperazine are 7-piperazinyl and 7-piperadinyl-3,4-dihydroquinazolin-2(1H)-ones that exhibit D 2 and 5-HT 1A receptor binding affinities, making them suitable for use as the active ingredient of pharmaceuticals for the treatment of schizophrenia. The derivatives have the general formula: where X is carbon or nitrogen and R is a group selected from a through f having the formula: or a pharmaceutically acceptable salt thereof. The piperazine compounds are prepared by condensing 4-bromo-2-nitro-benzonitrile with 1-Boc-piperazine (1-tert-butoxycarbonyl-piperazine) to form an intermediate that is converted to a piperazinyl-3,4-dihydroquinazolin-2(1H)-one. Subsequent reductive amination with the biarylaldehydes a through f completes the synthesis of the 7-piperadinyl-3,4-dihydroquinazolin-2(1H)-ones. The piperadinyl compounds are prepared from tert-butyl-4-(2-oxo-1,2,3,4-tetradihydroquinazolin-7-yl)piperidine-1-carboxylate, which is converted to 7-(piperidin-4-yl)-3,4-dihyroquinazolin-2(1H)-one. Subsequent reductive amination with the biarylaldehydes a through f completes the synthesis of the 7-piperidinyl-3,4-dihydroquinazolin-2(1H)-ones.

  哌啶和哌嗪的二氢喹啉衍生物是7-哌嗪基和7-哌啶基-3,4-二氢喹唑啉-2(1H)-酮，具有D2和5-HT1A受体结合亲和力，适合用作治疗精神分裂症的药物的活性成分。这些衍生物的通用公式为：其中X为碳或氮，R为从a到f的选择性基团，其公式为：或其药学上可接受的盐。哌嗪类化合物是通过将4-溴-2-硝基苯腈与1-Boc-哌嗪(1-叔丁氧羰基哌嗪)缩合形成中间体，然后转化为哌嗪基-3,4-二氢喹唑啉-2(1H)-酮来制备的。随后，与双芳基醛a到f进行还原胺化反应，完成了7-哌嗪基-3,4-二氢喹唑啉-2(1H)-酮的合成。哌啶类化合物是从叔丁基-4-(2-氧代-1,2,3,4-四氢喹唑啉-7-基)哌啶-1-羧酸酯开始制备的，该化合物转化为7-(哌啶-4-基)-3,4-二氢喹唑啉-2(1H)-酮。随后，与双芳基醛a到f进行还原胺化反应，完成了7-哌啶基-3,4-二氢喹唑啉-2(1H)-酮的合成。