5-nitro-2-(quinolin-8-yl)isoindoline-1,3-dione | 1370731-18-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 5-nitro-2-(quinolin-8-yl)isoindoline-1,3-dione
• CAS: 1370731-18-2
• 化学式: C₁₇H₉N₃O₄
• 分子量: 319.276
• InChiKey: QQCFEPMQTHEXIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.94
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  93.41
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-nitro-2-(quinolin-8-yl)isoindoline-1,3-dione 在 palladium on activated charcoal 、 氢气 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以221 mg的产率得到5-amino-2-(quinolin-8-yl)isoindoline-1,3-dione
  参考文献：
  名称：

  Wnt Inhibition Correlates with Human Embryonic Stem Cell Cardiomyogenesis: A Structure–Activity Relationship Study Based on Inhibitors for the Wnt Response

  摘要：

  Human embryonic stem cell-based high-content screening of 550 known signal transduction modulators showed that one "lead" (1, a recently described inhibitor of the proteolytic degradation of Axin) stimulated cardiomyogenesis. Because Axin controls canonical Wnt signaling, we conducted an investigation to determine whether the cardiogenic activity of 1 is Wnt-dependent, and we developed a structure-activity relationship to optimize the cardiogenic properties of 1. We prepared analogues with a range of potencies (low nanomolar to inactive) for Wnt/beta-catenin inhibition and for cardiogenic induction. Both functional activities correlated positively (r(2) = 0.72). The optimal compounds induced cardiogenesis 1.5-fold greater than 1 at 30-fold lower concentrations. In contrast, no correlation was observed for cardiogenesis and modulation of transforming growth factor beta (TGF beta)/Smad signaling that prominently influences cardiogenesis. Taken together, these data show that Wnt signaling inhibition is essential for cardiogenic activity and that the pathway can be targeted for the design of druglike cardiogenic molecules.

  DOI：

  10.1021/jm2010223
• 作为产物：
  描述：

  8-氨基喹啉 、 4-硝基邻苯二甲酸酐 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以230 mg的产率得到5-nitro-2-(quinolin-8-yl)isoindoline-1,3-dione
  参考文献：
  名称：

  Wnt Inhibition Correlates with Human Embryonic Stem Cell Cardiomyogenesis: A Structure–Activity Relationship Study Based on Inhibitors for the Wnt Response

  摘要：

  Human embryonic stem cell-based high-content screening of 550 known signal transduction modulators showed that one "lead" (1, a recently described inhibitor of the proteolytic degradation of Axin) stimulated cardiomyogenesis. Because Axin controls canonical Wnt signaling, we conducted an investigation to determine whether the cardiogenic activity of 1 is Wnt-dependent, and we developed a structure-activity relationship to optimize the cardiogenic properties of 1. We prepared analogues with a range of potencies (low nanomolar to inactive) for Wnt/beta-catenin inhibition and for cardiogenic induction. Both functional activities correlated positively (r(2) = 0.72). The optimal compounds induced cardiogenesis 1.5-fold greater than 1 at 30-fold lower concentrations. In contrast, no correlation was observed for cardiogenesis and modulation of transforming growth factor beta (TGF beta)/Smad signaling that prominently influences cardiogenesis. Taken together, these data show that Wnt signaling inhibition is essential for cardiogenic activity and that the pathway can be targeted for the design of druglike cardiogenic molecules.

  DOI：

  10.1021/jm2010223

文献信息

• Site-selective C–H bond carbonylation with CO₂ and cobalt-catalysis
  作者：Nagaraju Barsu、Deepti Kalsi、Basker Sundararaju

  DOI：10.1039/c8cy02060d

  日期：——

  in situ-produced CO gas for C–H bond carbonylation using earth-abundant cobalt catalysts. The ease of handling CO2 gas at atmospheric pressure allows us to prepare 13C labelled compounds which are otherwise difficult to achieve. The procedure developed makes it possible to utilize CO2 as a CO source, which can be widely applied as a C1 synthon that can be incorporated between C–H and N–H bonds of aromatic

  利用人为产生的温室气体CO 2通过转化为像CO这样的基本有价值的C1合成子来形成催化C-C键非常具有挑战性。能够将CO 2转化为CO并激活惰性C–H键的高效催化剂的需求是瓶颈。我们在本文中展示了一种在两腔系统中完成的串联方法，该方法可使用乙硅烷作为脱氧剂，并有效地利用氟化物介导的CO 2从CO 2高效生成CO，并利用大量存在的原位生成的CO气用于CH键的羰基化钴催化剂。在大气压下易于处理CO 2气体使我们可以制备13C标记的化合物，否则很难实现。所开发的方法使得利用CO 2作为CO源成为可能，该CO 2可以广泛用作C1合成子，可以结合在芳族，杂芳族和脂族羧酰胺的C–H和N–H键之间，以合成以位点选择性的方式包括螺环在内的各种环状酰亚胺。已证明了众所周知的血管紧张素受体阻滞剂（ARB）替米沙坦和一种众所周知的极低密度脂蛋白（VLDLs）药物吉非贝齐（Gemfibrozil）的后期衍生。此外，
• Copper-promoted site-selective carbonylation of sp³ and sp² C–H bonds with nitromethane
  作者：Xuesong Wu、Jinmin Miao、Yanrong Li、Guigen Li、Haibo Ge

  DOI：10.1039/c6sc01087c

  日期：——

  Copper-promoted direct carbonylation of unactivated sp3 C–H and aromatic sp2 C–H bonds of amides was developed using nitromethane as a novel carbonyl source. The sp3 C–H functionalization showed high site-selectivity by favoring the C–H bonds of α-methyl groups. The sp2 C–H carbonylation featured high regioselectivity and good functional group compatibility. Kinetic isotope effect studies indicated

  使用硝基甲烷作为新型羰基来源，开发了铜促进未活化的sp 3 C–H和酰胺的芳香族sp 2 C–H键的直接羰基化反应。sp 3 C–H官能化通过偏爱α-甲基的C–H键表现出较高的位点选择性。sp 2 C–H羰基化具有较高的区域选择性和良好的官能团相容性。动力学同位素效应研究表明，sp 3 C–H键断裂步骤是可逆的，而sp 2 C–H键断裂是不可逆的，但不是决定速率的步骤。对照实验表明，硝基甲基中间体应参与本反应。
• Oxidative C–H/N–H Carbonylation of Benzamide by Nickel Catalysis with CO as the Carbonyl Source
  作者：Chen Kang、Jiawei Xu、Xuan Li、Shoucai Wang、Guangbin Jiang、Fanghua Ji

  DOI：10.1021/acs.joc.2c00673

  日期：2022.8.5

  An efficient and direct carbonylation of aminoquinoline benzamides has been developed using abundant and inexpensive Ni(OAc)2·4H2O as the catalyst and carbon monoxide as a cost-efficient C1 building block. This process features good functional-group tolerance and can be conducted on gram scale. The directing group can be easily removed under mild conditions.

  使用丰富且廉价的 Ni(OAc) 2 ·4H 2 O 作为催化剂和一氧化碳作为具有成本效益的 C1 结构单元，开发了一种高效和直接的氨基喹啉苯甲酰胺羰基化反应。该过程具有良好的官能团耐受性，可以在克级进行。在温和的条件下可以很容易地去除导向基团。
• 一种镍催化的羰基化反应生成N-取代邻苯二甲酰亚胺类化合物的方法
  申请人：桂林理工大学

  公开号：CN114437028A

  公开（公告）日：2022-05-06

  本发明涉及一种镍催化的羰基化反应生成N‑取代邻苯二甲酰亚胺类化合物的方法。该方法是在反应容器中，加入8‑苯甲酰基氨基喹啉类化合物、催化剂、氧化剂、添加剂，用溶剂溶解，在玻璃试管上套上充有一氧化碳气体的气球，在40～150℃搅拌反应1‑40小时，反应结束后冷却至室温，拆除气球，反应液过滤，减压蒸除溶剂后，得粗产物，经柱层析提纯得到所述的N‑取代邻苯二甲酰亚胺类化合物。本发明利用镍催化的羰基化反应生成N‑取代邻苯二甲酰亚胺类化合物的方法，具有反应条件温和、操作简洁、底物适用范围广，产率优良等特点，对于邻苯二甲酰亚胺及其衍生物的合成与制备具有重要研究价值。
• 10.1021/acs.orglett.6b0311
  作者：Ni, Jiabin、Li, Jie、Fan, Zhoulong、Zhang, Ao

  DOI：10.1021/acs.orglett.6b0311

  日期：——