2-(furan-2-yl)thiazole-4-carbaldehyde | 1183430-59-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(furan-2-yl)thiazole-4-carbaldehyde
• 英文别名: 2-(Furan-2-yl)-1,3-thiazole-4-carbaldehyde
• CAS: 1183430-59-2
• 化学式: C₈H₅NO₂S
• mdl: MFCD12776046
• 分子量: 179.199
• InChiKey: CICRHHYRKYJFCY-UHFFFAOYSA-N

物化性质

• 沸点：
  335.3±40.0 °C(Predicted)
• 密度：
  1.358±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(furan-2-yl)thiazole-4-carbaldehyde 、 N-去异丙基普萘洛尔 在 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  GPCR 的片段进化：二级结合位点在优化中的作用

  摘要：

  我们开发了一种基于对接的片段进化方法，将正构片段扩展到不太保守的 GPCR 二级结合口袋。我们合成并测试了 112 个双位分子，评估了 13 000 次 β 1 - 和 β 2 -肾上腺素能受体的延伸。我们的结果证实了二级结合口袋对效力和选择性优化的积极贡献。

  DOI：

  10.1039/d1cc04636e
• 作为产物：
  描述：

  2-呋喃硼酸 、 2-溴-4-醛基噻唑 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 乙醇 为溶剂， 反应 24.0h， 以73%的产率得到2-(furan-2-yl)thiazole-4-carbaldehyde
  参考文献：
  名称：

  Thiazolidine derivatives as potent and selective inhibitors of the PIM kinase family

  摘要：

  The PIM family of serine/threonine kinases have become an attractive target for anti-cancer drug development, particularly for certain hematological malignancies. Here, we describe the discovery of a series of inhibitors of the PIM kinase family using a high throughput screening strategy. Through a combination of molecular modeling and optimization studies, the intrinsic potencies and molecular properties of this series of compounds was significantly improved. An excellent pan-PIM isoform inhibition profile was observed across the series, while optimized examples show good selectivity over other kinases. Two PIM-expressing leukemic cancer cell lines, MV4-11 and 1(562, were employed to evaluate the in vitro anti-proliferative effects of selected inhibitors. Encouraging activities were observed for many examples, with the best example (44) giving an IC55 of 0.75 mu M against the K562 cell line. These data provide a promising starting point for further development of this series as a new cancer therapy through PIM kinase inhibition. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.02.056

文献信息

• WO2020069625A5
  申请人：——

  公开号：WO2020069625A5

  公开（公告）日：2022-10-11
• TRANSCRIPTION FACTOR BRN2 INHIBITORY COMPOUNDS AS THERAPEUTICS AND METHODS FOR THEIR USE
  申请人：The University of British Columbia

  公开号：EP3860994A1

  公开（公告）日：2021-08-11
• [EN] TRANSCRIPTION FACTOR BRN2 INHIBITORY COMPOUNDS AS THERAPEUTICS AND METHODS FOR THEIR USE<br/>[FR] COMPOSÉS INHIBITEURS DU FACTEUR DE TRANSCRIPTION BRN2 UTILISÉS EN TANT QU'AGENTS THÉRAPEUTIQUES ET LEURS PROCÉDÉS D'UTILISATION
  申请人：UNIV BRITISH COLUMBIA

  公开号：WO2020069625A1

  公开（公告）日：2020-04-09

  The invention provides a variety of compounds having the structure of Formula I and uses of such compounds for treatment of various indications, including cancer as well as methods of treatment involving such compounds are also provided. The uses of the compounds may specifically include: bladder cancer, cholangiocarcinoma; colorectal cancer; diffuse large B-cell lymphoma (DLBC); liver cancer; ovarian cancer; thymoma; thyroid cancer; clear cell renal cell carcinoma (CCRCC); chromophobe renal cell carcinoma (ChRCC); prostate cancer; breast cancer; uterine cancer; pancreatic cancer; cervical cancer; uveal melanoma; acute myeloid leukemia (AML); head and neck cancer; small cell lung cancer (SCLC); lung adenocarcinoma sarcoma; mesothelioma; adenoid cystic carcinoma (ACC), sarcoma; testicular germ cell cancer; uterine cancer; pheochromocytoma and paraganglioma (PCPG); melanoma; glioma; glioblastoma multiforme; T-cell Acute Lymphoblastic Leukemia; T-cell Lympohoma, medulloblastoma; and neuroblastoma.
• Thiazolidine derivatives as potent and selective inhibitors of the PIM kinase family
  作者：Carole J.R. Bataille、Méabh B. Brennan、Simon Byrne、Stephen G. Davies、Matthew Durbin、Oleg Fedorov、Kilian V.M. Huber、Alan M. Jones、Stefan Knapp、Gu Liu、Anna Nadali、Camilo E. Quevedo、Angela J. Russell、Roderick G. Walker、Robert Westwood、Graham M. Wynne

  DOI：10.1016/j.bmc.2017.02.056

  日期：2017.5

  The PIM family of serine/threonine kinases have become an attractive target for anti-cancer drug development, particularly for certain hematological malignancies. Here, we describe the discovery of a series of inhibitors of the PIM kinase family using a high throughput screening strategy. Through a combination of molecular modeling and optimization studies, the intrinsic potencies and molecular properties of this series of compounds was significantly improved. An excellent pan-PIM isoform inhibition profile was observed across the series, while optimized examples show good selectivity over other kinases. Two PIM-expressing leukemic cancer cell lines, MV4-11 and 1(562, were employed to evaluate the in vitro anti-proliferative effects of selected inhibitors. Encouraging activities were observed for many examples, with the best example (44) giving an IC55 of 0.75 mu M against the K562 cell line. These data provide a promising starting point for further development of this series as a new cancer therapy through PIM kinase inhibition. (C) 2017 Elsevier Ltd. All rights reserved.
• Fragment evolution for GPCRs: the role of secondary binding sites in optimization
  作者：Florent Chevillard、Ádám Kelemen、Jillian G. Baker、Vivien A. Aranyodi、Frank Balzer、Peter Kolb、György M. Keserű

  DOI：10.1039/d1cc04636e

  日期：——

  We developed a docking-based fragment evolution approach that extends orthosteric fragments towards a less conserved secondary binding pocket of GPCRs. Evaluating 13 000 extensions for the β1- and β2-adrenergic receptors we synthesized and tested 112 bitopic molecules. Our results confirmed the positive contribution of the secondary binding pocket to both potency and selectivity optimizations.

  我们开发了一种基于对接的片段进化方法，将正构片段扩展到不太保守的 GPCR 二级结合口袋。我们合成并测试了 112 个双位分子，评估了 13 000 次 β 1 - 和 β 2 -肾上腺素能受体的延伸。我们的结果证实了二级结合口袋对效力和选择性优化的积极贡献。