6-bromo-8-isopropyl-2,2-dimethylchromane | 1220476-09-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6-bromo-8-isopropyl-2,2-dimethylchromane
• 英文别名: CSIC-E183；6-Bromo-8-isopropyl-2,2-dimethylchroman；6-bromo-2,2-dimethyl-8-propan-2-yl-3,4-dihydrochromene
• CAS: 1220476-09-4
• 化学式: C₁₄H₁₉BrO
• 分子量: 283.208
• InChiKey: GBOOQCQGXPVZIT-UHFFFAOYSA-N

物化性质

• 沸点：
  326.1±41.0 °C(Predicted)
• 密度：
  1.220±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-bromo-8-isopropyl-2,2-dimethylchromane 在 叔丁基锂 、 sodium hydroxide 作用下， 生成 8-isopropyl-2,2-dimethylchroman-6-carboxylic acid
  参考文献：
  名称：

  Development of Chromanes as Novel Inhibitors of the Uncoupling Proteins

  摘要：

  The uncoupling proteins (UCPs) are mitochondrial carriers that modulate the energetic efficiency and, as a result, can lower superoxide levels. Here, we describe the discovery of a small-molecule inhibitor of the UCPs. Screening of potential UCP1 regulators led to the identification of chromane derivatives that inhibit its proton conductance. Members of the UCP family can act as a defense against oxidative stress and, thus, UCP2 plays a protective role in tumor cells. High UCP2 levels have been associated with chemoresistance. We demonstrate that chromanes also inhibit UCP2 and, in HT-29 human carcinoma cells, cause oxidative stress. The chromane derivatives can act synergistically with chemotherapeutic agents; for instance, they increase the toxicity of arsenic trioxide in HT-29 cells. These findings open a promising line in the development of novel anticancer agents.

  DOI：

  10.1016/j.chembiol.2010.12.012

文献信息

• [EN] CHROMAN DERIVATIVES AND USES THEREOF AS INHIBITORS OF THE ACTIVITY OF DECOUPLING PROTEINS<br/>[ES] DERIVADOS DE CROMANO Y SUS USOS COMO INHIBIDORES DE LA ACTIVIDAD DE LAS PROTEÍNAS DESACOPLANTES<br/>[FR] DÉRIVÉS DE CHROMANE ET UTILISATIONS DE CES DERNIERS EN TANT QU'INHIBITEURS DE L'ACTIVITÉ DES PROTÉINES DÉCOUPLANTES
  申请人：CONSEJO SUPERIOR INVESTIGACION

  公开号：WO2010037886A1

  公开（公告）日：2010-04-08

  Compuestos derivados del cromano, que presentan Ia fórmula general (I), donde, R1 y R2, son iguales o diferentes entre sí, y están representados por un átomo de hidrógeno (H) o un grupo alquilo (C1-C8); R3 está representado por un átomo de H, un halógeno, un grupo arilo o un grupo -COOR5; donde R5 es alquilo (C1-C4) o un alquilarilo; y R4 está representado por un átomo de hidrógeno (H), un grupo alquilarilo o un grupo alquilo (C1-C8), lineal o ramificado. Así como sus diferentes usos, más concretamente en la identificación de compuestos terapéuticos, como compuestos reguladores de las proteínas desacoplantes o su uso terapéutico para el tratamiento de diferentes enfermedades y dolencias que cursen con un aumento en la actividad de dichas proteínas
• Development of Chromanes as Novel Inhibitors of the Uncoupling Proteins
  作者：Eduardo Rial、Leonor Rodríguez-Sánchez、Patricio Aller、Arancha Guisado、M. Mar González-Barroso、Eunate Gallardo-Vara、Mariano Redondo-Horcajo、Esther Castellanos、Roberto Fernández de la Pradilla、Alma Viso

  DOI：10.1016/j.chembiol.2010.12.012

  日期：2011.2

  The uncoupling proteins (UCPs) are mitochondrial carriers that modulate the energetic efficiency and, as a result, can lower superoxide levels. Here, we describe the discovery of a small-molecule inhibitor of the UCPs. Screening of potential UCP1 regulators led to the identification of chromane derivatives that inhibit its proton conductance. Members of the UCP family can act as a defense against oxidative stress and, thus, UCP2 plays a protective role in tumor cells. High UCP2 levels have been associated with chemoresistance. We demonstrate that chromanes also inhibit UCP2 and, in HT-29 human carcinoma cells, cause oxidative stress. The chromane derivatives can act synergistically with chemotherapeutic agents; for instance, they increase the toxicity of arsenic trioxide in HT-29 cells. These findings open a promising line in the development of novel anticancer agents.