5-bromo-3-chloro-2-methoxybenzaldehyde | 25299-27-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-bromo-3-chloro-2-methoxybenzaldehyde
• CAS: 25299-27-8
• 化学式: C₈H₆BrClO₂
• mdl: MFCD03031750
• 分子量: 249.491
• InChiKey: TYMYZNFVODWIOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-bromo-3-chloro-2-methoxybenzaldehyde 在 potassium permanganate 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 48.0h， 生成 methyl 5-bromo-3-chloro-2-methoxybenzoate
  参考文献：
  名称：

  Design, Synthesis, Anti-HIV Activities, and Metabolic Stabilities of Alkenyldiarylmethane (ADAM) Non-nucleoside Reverse Transcriptase Inhibitors

  摘要：

  The alkenyldiarylmethane (ADAM) HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs) are effective anti-HIV agents in cell culture. However, the potential clinical utility of the ADAMs is expected to be limited by the presence of methyl ester moieties that are likely to be metabolized by nonspecific esterases in blood plasma to biologically inactive carboxylic acid derivatives. The present investigation was therefore undertaken to investigate the anti-HIV activities of the ADAMs versus HIV-1(IIIB) and HIV-2(ROD) in MT-4 cells and the stabilities of the biologically active ADAMs in rat plasma. The ADAMs displayed a wide range of metabolic stabilities in rat plasma, with half-lives ranging from 0.9 to 76.6 min. A wide assortment of structural modifications was tolerated, with 18 of the 32 compounds tested displaying EC50 values between 0.3 and 3.7 muM versus HIV-1(IIIB) in MT-4 cells, 3 compounds in the EC50 = 13.2-35.4 muM range, and the remaining compounds inactive. Consistent with the mechanism of action of the ADAMs as NNRTIs, they were inactive or displayed comparatively low activity versus HIV-2ROD. The replacement of the two aromatic methyl ester substituents in one of the most active ADAMs (EC50 = 0.6 muM) with two methyl thioester groups resulted in an increase in plasma half-life from 5.8 to 55.3 min, while maintaining the antiviral potency at the EC50 = 1.8 muM level. At the same time, the bis(thioester) modification was less cytotoxic to uninfected MT-4 cells, with a CC50 of >224 muM versus 160 muM for the parent compound.

  DOI：

  10.1021/jm049916x
• 作为产物：
  描述：

  4-溴-2-氯苯酚 在 potassium carbonate 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 44.0h， 生成 5-bromo-3-chloro-2-methoxybenzaldehyde
  参考文献：
  名称：

  Design, Synthesis, Anti-HIV Activities, and Metabolic Stabilities of Alkenyldiarylmethane (ADAM) Non-nucleoside Reverse Transcriptase Inhibitors

  摘要：

  The alkenyldiarylmethane (ADAM) HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs) are effective anti-HIV agents in cell culture. However, the potential clinical utility of the ADAMs is expected to be limited by the presence of methyl ester moieties that are likely to be metabolized by nonspecific esterases in blood plasma to biologically inactive carboxylic acid derivatives. The present investigation was therefore undertaken to investigate the anti-HIV activities of the ADAMs versus HIV-1(IIIB) and HIV-2(ROD) in MT-4 cells and the stabilities of the biologically active ADAMs in rat plasma. The ADAMs displayed a wide range of metabolic stabilities in rat plasma, with half-lives ranging from 0.9 to 76.6 min. A wide assortment of structural modifications was tolerated, with 18 of the 32 compounds tested displaying EC50 values between 0.3 and 3.7 muM versus HIV-1(IIIB) in MT-4 cells, 3 compounds in the EC50 = 13.2-35.4 muM range, and the remaining compounds inactive. Consistent with the mechanism of action of the ADAMs as NNRTIs, they were inactive or displayed comparatively low activity versus HIV-2ROD. The replacement of the two aromatic methyl ester substituents in one of the most active ADAMs (EC50 = 0.6 muM) with two methyl thioester groups resulted in an increase in plasma half-life from 5.8 to 55.3 min, while maintaining the antiviral potency at the EC50 = 1.8 muM level. At the same time, the bis(thioester) modification was less cytotoxic to uninfected MT-4 cells, with a CC50 of >224 muM versus 160 muM for the parent compound.

  DOI：

  10.1021/jm049916x

文献信息

• 一种二-三芳胺取代膦氧基苯并菲类化合物、中 间体及制备方法与应用
  申请人：昆山维信诺显示技术有限公司

  公开号：CN103183711B

  公开（公告）日：2016-04-20

  本发明涉及一种带有磷氧官能团以及三芳胺官能团的双极性有机材料。此类化合物通式如下式(Pn)所示，Ar1、Ar2、Ar3、Ar4和Ar5彼此独立地为芳基或杂芳基；R1～R4彼此独立地为氢、烷基、烷氧基、环烷基、芳基、或杂芳基。本发明的双极性化合物，作为三重态发光染料的主体材料或者载流子传输材料使用，其具备高载流子传输能力、高稳定性的特点，同时，既能够传输电子又能够传输空穴，有效地保证了发光层的电荷传输平衡，提高相应有机电致发光器件的亮度和效率，改善有机电致发光器件的寿命，克服器件在大电流下的效率低和寿命短的缺点。
• Boron Containing PDE4 Inhibitors
  申请人：Pfizer Inc.

  公开号：US20200108083A1

  公开（公告）日：2020-04-09

  The present invention relates to boron containing compounds of Formula (I) X—Y—Z   Formula (I) that inhibit phosphodiesterase 4 (PDE4). The invention also encompasses pharmaceutical compositions containing these compounds and methods for treating diseases, conditions, or disorders ameliorated by inhibition of PDE4.

  本发明涉及具有化学式（I）X—Y—Z的含硼化合物，化学式（I）抑制磷酸二酯酶4（PDE4）。该发明还涵盖含有这些化合物的药物组合物以及通过抑制PDE4治疗疾病、症状或障碍的方法。
• N-BENZYLANILINE DERIVATIVE AND USES THEREOF
  申请人：Nanjing Medical University

  公开号：US20140303248A1

  公开（公告）日：2014-10-09

  A N-benzylaniline derivative and uses thereof. The derivative is a compound represented by formula I or a pharmaceutically acceptable salt thereof. The compound protects against cerebral ischemia/reperfusion injury and has analgesic action for chronic pathologic pain, and may be used to treat cerebral apoplexy, neuropathic pain, and inflammatory pain. Moreover, because of the unique mechanism of action of the compound, the compound can be used to treat epilepsy, affective disorder, and neurodegenerative diseases.

  一种N-苄基苯胺衍生物及其用途。该衍生物是由式I表示的化合物或其药学上可接受的盐。该化合物对脑缺血/再灌注损伤具有保护作用，对慢性病理性疼痛具有镇痛作用，并可用于治疗脑卒中、神经病性疼痛和炎症性疼痛。此外，由于该化合物具有独特的作用机制，因此可以用于治疗癫痫、情感障碍和神经退行性疾病。
• PDE4 inhibitor (R)-4-(5-(4-methoxy-3-propoxyphenyl)pyridin-3-yl)-1,2-oxaborolan-2-ol
  申请人：Pfizer Inc.

  公开号：US10946031B2

  公开（公告）日：2021-03-16

  The present invention relates to PDE4 inhibitor (R)-4-(5-(4-methoxy-3-propoxyphenyl)pyridin-3-yl)-1,2-oxaborolan-2-ol including the crystalline monohydrate thereof.

  本发明涉及 PDE4 抑制剂 (R)-4-(5-(4-甲氧基-3-丙氧基苯基)吡啶-3-基)-1,2-氧硼戊环-2-醇，包括其结晶一水合物。
• BORON CONTAINING PDE4 INHIBITORS
  申请人：Pfizer Inc.

  公开号：EP3861001A1

  公开（公告）日：2021-08-11