4H-噻吩并[3,2-b]氮杂卓-5,8-二酮,6,7-二氢- | 137046-61-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4H-噻吩并[3,2-b]氮杂卓-5,8-二酮,6,7-二氢-
• 英文名称: 4H-thieno<3,2-b>azepine-5,8(6H,7H)-dione
• 英文别名: 6,7-dihydro-4H-thieno[3,2-b]azepine-5,8-dione；4H-thieno[3,2-b]azepine-5,8(6H,7H)-dione；6,7-dihydrothieno[3,2-b]azepin-5,8-dione
• CAS: 137046-61-8
• 化学式: C₈H₇NO₂S
• 分子量: 181.215
• InChiKey: JQIAMULIXYHWGW-UHFFFAOYSA-N

物化性质

• 沸点：
  416.0±40.0 °C(Predicted)
• 密度：
  1.367±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  74.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4H-噻吩并[3,2-b]氮杂卓-5,8-二酮,6,7-二氢- 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (4-nitrophenyl)(5,6,7,8-tetrahydro-4H-thieno[3,2-b]azepin-4-yl)methanone
  参考文献：
  名称：

  Regioselective Synthesis of Several Heterocyclic Fused Azepines Using Diisobutylaluminum Hydride

  摘要：

  5,6,7,8-Tetrahydrothieno[3,2-b]azepine,5,6,7,8-tetrahydro-1H-furo[3,- 2b]azepine, and 1,4,5,6,7,8-hexahydropyrrolo [3,2-b]azepine were synthesized by the ring expansion reaction of heterocyclic fused cyclohexanone oximes with diisobutylaluminum hydride (DIBAH). The mechanism of the reaction was different from that of Beckmann rearrangement.

  DOI：

  10.3987/com-98-8104
• 作为产物：
  描述：

  3-氨其噻吩-2-甲酸乙酯 在 potassium hydride 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 4H-噻吩并[3,2-b]氮杂卓-5,8-二酮,6,7-二氢-
  参考文献：
  名称：

  New thiophene analogues of kenpaullone: synthesis and biological evaluation in breast cancer cells

  摘要：

  Thieno analogues of kenpaullone have been synthesized using an established method. We investigated the effect of five structural analogues of kenpaullone on vincristine sensitive and resistant MCF7 (human mammary adenocarcinoma) cells. One analogue, 8-Bromo-6,11-dihydro-thermo-[3',2':2,3]azepino[4,5-b]indol-5(4H)-one (3a), showed an antiproliferative activity in the drug sensitive cell line that led to cell accumulation in G2/M phase. In addition, repression of cdk 1. a G2/M transition key regulator, as well as induction of p21 were observed at the mRNA level. Programmed cell death (apoptosis) was induced in early time treatments and was accompanied by p53 mRNA induction. The antiproliferative and proapoptotic properties of 3a make this CDK inhibitor an interesting candidate for further investigations. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.02.010

文献信息

• Design and synthesis of 1,5- and 2,5-substituted tetrahydrobenzazepinones as novel potent and selective integrin α V β 3 antagonists
  作者：Andreas Kling、Gisela Backfisch、Jürgen Delzer、Hervé Geneste、Claudia Graef、Wilfried Hornberger、Udo E.W Lange、Arnulf Lauterbach、Werner Seitz、Thomas Subkowski

  DOI：10.1016/s0968-0896(02)00616-8

  日期：2003.4

  linking guanidine moiety and core, and modification of the guanidine mimetic. These efforts led to the identification of novel alpha(V)beta(3) inhibitors displaying potency in the subnanomolar range, selectivity versus alpha(IIb)beta(3) and functional efficacy in relevant cellular assays. A method for the preparation of enantiomerically pure derivatives was developed, and respective enantiomers evaluated

  设计和合成基于1，5-或2，5-取代的四氢苯并enza庚因核心的新型整联蛋白α（V）β（3）拮抗剂。通过alpha（V）beta（3）结合测定法确定各个化合物的体外活性，并将选定的衍生物提交功能细胞测定法进一步表征。通过修饰苯并ze庚酮核心，改变连接胍部分和核心的间隔基以及修饰胍模拟物获得SAR。这些努力导致鉴定出新颖的alpha（V）beta（3）抑制剂，其在亚纳摩尔范围内显示效力，相对于alpha（IIb）beta（3）的选择性以及相关细胞测定中的功能功效。开发了制备对映体纯衍生物的方法，并在体外评估了各个对映体。
• Fused azepinone cyclin dependent kinase inhibitors
  申请人：——

  公开号：US20020042412A1

  公开（公告）日：2002-04-11

  A new class of cyclin dependent kinase inhibitors that also have antiproliferative activity in human tumor cell line assays are described. Most of these compounds satisfy the formula 1 wherein A is oxygen or sulfur coupled to the right by a single or double bond; R 2 is selected from the group consisting of hydrogen, aryl, lower aliphatic substituents, particularly alkyl and lower alkyl ester; R 4 -R 7 are independently selected from the group consisting of alkoxy, amino, acyl, aliphatic substituents, particularly alkyl, alkenyl and alkinyl substituents, aliphatic alcohols, particularly alkyl alcohols, aliphatic nitriles, particularly alkyl nitriles, cyano, nitro, carboxyl, halogen, hydrogen, hydroxyl, imino, and &agr;, &bgr;, unsaturated ketones; R 8 -R 11 are independently selected from the group consisting of aliphatic substituents, particularly alkyl, alkenyl and alkinyl substituents, particularly lower aliphatic substituents, alipahatic alcohols, particularly alkyl alcohols, alkoxy, acyl, cyano, nitro, epoxy, haloalkyl groups, halogen, hydrogen and hydroxyl; R 12 is selected from the group consisting of aliphatic groups, particularly lower alkyl groups, aliphatic alcohols, particularly alkyl alcohols, carboxylic acids and hydrogen. Compositions comprising effective amounts of such compounds also are described. These compounds and compositions can be used in a method for inhibiting the proliferation of living cells in a subject comprising administering an effective amount of the compound(s), or composition(s) comprising the compound(s), to a subject to inhibit the proliferation of living cells, such as neoplastic cells.

  描述了一类新型的细胞周期依赖性激酶抑制剂，这些抑制剂在人类肿瘤细胞系实验中还具有抗增殖活性。其中大多数化合物符合以下公式：其中A是氧或硫，通过单键或双键与右侧连接；R2选择自氢、芳基、较低的脂肪基取代物，特别是烷基和较低的烷基酯；R4-R7独立地选择自烷氧基、氨基、酰基、脂肪基取代物，特别是烷基、烯基和炔基取代物、脂肪醇，特别是烷基醇、脂肪腈，特别是烷基腈、氰基、硝基、羧基、卤素、氢、羟基、亚甲基、β-甲基、不饱和酮；R8-R11独立地选择自脂肪基取代物，特别是烷基、烯基和炔基取代物，特别是较低的脂肪基取代物、脂肪醇，特别是烷基醇、烷氧基、酰基、氰基、硝基、环氧基、卤代烷基、卤素、氢和羟基；R12选择自脂肪基，特别是较低烷基，脂肪醇，特别是烷基醇，羧酸和氢。还描述了包含这些化合物有效量的组合物。这些化合物和组合物可用于抑制体内细胞增殖的方法，包括向受体内施用化合物的有效量或含有该化合物的组合物的有效量，以抑制细胞增殖，如肿瘤细胞。
• Synthese von 7,12-Dihydro-indolo[3,2-d][1]benzazepin-6-(5H)-onen und 6,11-Dihydro-thieno-[3′,2′:2,3]azepino[4,5-b]indol-5(4H)-on
  作者：Conrad Kunick

  DOI：10.1002/ardp.19923250509

  日期：——

  Die Titelverbindungen 4 und 6 wurden durch Fischer‐Indol‐Synthese dargestellt. 4a wird durch Brom in Eisessig in 10‐Position substituiert. 4 und 6 zeigen eine schnelle Ringinversion des Azepinringes.

  标题化合物 4 和 6 通过 Fischer 吲哚合成制备。4a 在冰醋酸中的 10-位被溴取代。图4和6显示了氮杂环的快速环反转。
• Synthese [b]-kondensierter azepindione durch dealkoxycarbonylierung
  作者：Conrad Kunick

  DOI：10.1002/ardp.2503240910

  日期：——

  Synthesis of [b]‐Fused Azepinediones by Dealkoxycarbonylation

  通过脱烷氧基羰基化合成 [b]-稠合氮杂二酮
• [EN] FUSED AZEPINONE CYCLIN DEPENDENT KINASE INHIBITORS<br/>[FR] INHIBITEURS DE KINASES DEPENDANTES DE LA CYCLINE SOUS FORME D'AZEPINONE FUSIONNEE
  申请人：US HEALTH

  公开号：WO1999065910A1

  公开（公告）日：1999-12-23

  A new class of cyclin dependent kinase inhibitors that also have antiproliferative activity in human tumor cell line assays are described. Most of these compounds satisfy formula (I); wherein A is oxygen or sulfur coupled to the right by a single or double bond; R2 is selected from the group consisting of hydrogen, aryl, lower aliphatic substituents, particularly alkyl and lower alkyl ester; R4-R7 are independently selected from the group consisting of alkoxy, amino, acyl, aliphatic substituents, particularly alkyl, alkenyl and alkinyl substituents, aliphatic alcohols, particularly alkyl alcohols, aliphatic nitriles, particularly alkyl nitriles, cyano, nitro, carboxyl, halogen, hydrogen, hydroxyl, imino, and α, β unsaturated ketones; R8-R11 are independently selected from the group consisting of aliphatic substituents, particularly alkyl, alkenyl and alkinyl substituents, particularly lower aliphatic substituents, aliphatic alcohols, particularly alkyl alcohols, alkoxy, acyl, cyano, nitro, epoxy, haloalkyl groups, halogen, hydrogen and hydroxyl; R12 is selected from the group consisting of aliphatic groups, particularly lower alkyl groups, aliphatic alcohols, particularly alkyl alcohols, carboxylic acids and hydrogen. Compositions comprising effective amounts of such compounds also are described. These compounds and compositions can be used in a method for inhibiting the proliferation of living cells in a subject comprising administering an effective amount of the compound(s), or composition(s) comprising the compound(s), to a subject to inhibit the proliferation of living cells, such as neoplastic cells.

  描述了一类新型的细胞周期依赖性激酶抑制剂，这些化合物在人类肿瘤细胞系试验中也具有抗增殖活性。其中大多数化合物满足公式（I）; 其中A是氧或硫，通过单键或双键与右侧相连; R2选自氢、芳基、较低的脂肪基取代基，特别是烷基和较低的烷基酯基; R4-R7独立地选自烷氧基、氨基、酰基、脂肪基取代基，特别是烷基、烯基和炔基取代基，脂肪醇，特别是烷基醇，脂肪腈，特别是烷基腈，氰基，硝基，羧基，卤素，氢，羟基，亚氨基和α，β不饱和酮; R8-R11独立地选自脂肪基取代基，特别是烷基、烯基和炔基取代基，特别是较低的脂肪基取代基，脂肪醇，特别是烷基醇，烷氧基，酰基，氰基，硝基，环氧基，卤代烷基，卤素，氢和羟基; R12选自脂肪基，特别是较低的烷基，脂肪醇，特别是烷基醇，羧酸和氢的群。还描述了包含这些化合物有效量的组合物。这些化合物和组合物可用于抑制受试主体中细胞增殖的方法，包括向受试主体施用化合物的有效量或含有化合物的组合物的有效量，以抑制细胞增殖，例如肿瘤细胞。