(3-nitrophenyl)methanesulfonic acid | 553666-72-1

• 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: (3-nitrophenyl)methanesulfonic acid
• 英文别名: (3-Nitro-phenyl)-methansulfonsaeure
• CAS: 553666-72-1
• 化学式: C₇H₇NO₅S
• 分子量: 217.202
• InChiKey: FLKHMTSGHUOTCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3-nitrophenyl)methanesulfonic acid 在 镍 氢气 作用下， 以 水 为溶剂， 以82%的产率得到(3-aminophenyl)methanesulfonic acid
  参考文献：
  名称：

  轻松合成4-和6-氯甲基-1 H-吲哚-2-羧酸酯：用氯代替磺酸官能团

  摘要：

  通过分别从2-乙氧基羰基-1 H-吲哚-4-或6-甲磺酸中消除SO 2来制备有价值的新型合成中间体4-或6-氯甲基-1 H-吲哚-2-羧酸，可通过费歇尔式的模糊化技术轻松访问。

  DOI：

  10.1016/s0040-4039(03)00327-7
• 作为产物：
  描述：

  间硝基氯化苄 在 sodium sulfite 作用下， 生成 (3-nitrophenyl)methanesulfonic acid
  参考文献：
  名称：

  Weiss; Reiter, Justus Liebigs Annalen der Chemie, 1907, vol. 355, p. 185

  摘要：

  DOI：

文献信息

• Discovery and Characterization of XY101, a Potent, Selective, and Orally Bioavailable RORγ Inverse Agonist for Treatment of Castration-Resistant Prostate Cancer
  作者：Yan Zhang、Xishan Wu、Xiaoqian Xue、Chenchang Li、Junjian Wang、Rui Wang、Cheng Zhang、Chao Wang、Yudan Shi、Lingjiao Zou、Qiu Li、Zenghong Huang、Xiaojuan Hao、Kerry Loomes、Donghai Wu、Hong-Wu Chen、Jinxin Xu、Yong Xu

  DOI：10.1021/acs.jmedchem.9b00327

  日期：2019.5.9

  complex with the RORγ ligand binding domain provided a solid structural basis for its antagonistic mechanism. 27 potently inhibited cell growth, colony formation, and the expression of AR, AR-V7, and PSA. 27 also exhibited good metabolic stability and a pharmacokinetic profile with oral bioavailability of 59% and a half-life of 7.3 h. Notably, 27 demonstrated promising therapeutic effects with significant

  我们报告了核受体RORγ反向激动剂作为前列腺癌治疗药物的设计，优化和生物学评估。最有效的化合物27（指定为XY101）在基于细胞的报告基因分析中表现出细胞活性，IC50值为30 nM，对其他核受体亚型具有良好的选择性。27与RORγ配体结合域复合的共晶体结构为其拮抗机制提供了坚实的结构基础。27有效抑制细胞生长，集落形成以及AR，AR-V7和PSA的表达。27还表现出良好的代谢稳定性和药代动力学特征，口服生物利用度为59％，半衰期为7.3小时。尤其，图27显示了在小鼠的前列腺癌异种移植模型中具有显着的肿瘤生长抑制作用的有希望的治疗作用。有效的，选择性的，代谢稳定的和口服可用的RORγ反向激动剂代表了一类新型化合物，可作为对抗前列腺癌的潜在疗法。
• Process for production of delta-9- tetrahydrocannabinol
  申请人：Burdick C. David

  公开号：US20070093665A1

  公开（公告）日：2007-04-26

  The present invention relates to a process for preparation of a delta-9-tetrahydrocannabinol compound or derivative thereof involving treating a first intermediate compound with an organoaluminum-based Lewis acid catalyst, under conditions effective to produce the delta-9-tetrahydrocannabinol compound or derivative thereof. Another aspect of the present invention relates to a process for preparation of a cannabidiol or cannabidiolate compound involving reacting a first starting compound with a second starting compound in the presence of a metal triflate catalyst, under conditions effective to form the cannabidiol or cannabidiolate compound. The present invention also relates to a compound of the formula: where R 8 , R 9 , and R 10 are the same or different and independently selected from the group consisting of H, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or halo, with R 1 , R 2 , and R 3 defined herein.

  本发明涉及一种制备Δ-9-四氢大麻酚化合物或其衍生物的方法，涉及将第一中间化合物与基于有机铝的Lewis酸催化剂处理，在有效条件下产生Δ-9-四氢大麻酚化合物或其衍生物。本发明的另一个方面涉及一种制备大麻二酚或大麻二酚盐化合物的方法，涉及在金属三氟甲磺酸盐催化剂存在下，将第一起始化合物与第二起始化合物反应，在有效条件下形成大麻二酚或大麻二酚盐化合物。本发明还涉及一个化合物，其化学式为：其中R8、R9和R10相同或不同，并且独立地选自H、取代或未取代的烷基、取代或未取代的芳基、取代或未取代的杂环芳基或卤素，其中R1、R2和R3在此定义。
• Processes for the production of cannabidiol derivatives and intermediates thereof
  申请人：Albany Molecular Research, Inc.

  公开号：EP2578561A1

  公开（公告）日：2013-04-10

  This invention relates to a process for the preparation of a product compound of the formula: wherein: R1 is H, substituted or unsubstituted alkyl, carboxylic ester, or acyl; R2 is H, OH, protected hydroxyl, substituted or unsubstituted alkyl, alkenyl, alkynyl, acyl, aryl, or heteroaryl; R3 is H, substituted or unsubstituted alkyl, carboxylic ester, or acyl; R4 is H, substituted or unsubstituted alkyl, silyl, hetero-substituted or unsubstituted acyl, alkylsulfonyl, arylsulfonyl, alkylphosphoryl, or arylphosphoryl; and R6 is H, substituted or unsubstituted alkyl, silyl, hetero-substituted or unsubstituted acyl, alkylsulfonyl, arylsulfonyl, alkylphosphoryl, or arylphosphoryl.

  本发明涉及一种制备公式化合物的过程：其中：R1为氢，取代或未取代烷基，羧酸酯或酰基；R2为氢，羟基，保护羟基，取代或未取代烷基，烯基，炔基，酰基，芳基或杂环芳基；R3为氢，取代或未取代烷基，羧酸酯或酰基；R4为氢，取代或未取代烷基，硅基，杂原子取代或未取代酰基，烷基磺酰基，芳基磺酰基，烷基磷酰基或芳基磷酰基；R6为氢，取代或未取代烷基，硅基，杂原子取代或未取代酰基，烷基磺酰基，芳基磺酰基，烷基磷酰基或芳基磷酰基。
• Sulfonyl esters of tetrahydrocannabinol and derivatives thereof
  申请人：Albany Molecular Research, Inc.

  公开号：EP2578577A1

  公开（公告）日：2013-04-10

  This invention relates to a compound of the formula: wherein: R1 is H, substituted or unsubstituted alkyl, carboxylic ester, or acyl; R2 is H, OH, protected hydroxyl, substituted or unsubstituted alkyl, alkenyl, alkynyl, acyl, aryl, or heteroaryl; R3 is H, substituted or unsubstituted alkyl, carboxylic ester, or acyl; R8, R9, and R10 are the same or different and independently selected from the group consisting of H, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or halo; and R8 and R9; R8 and R10; or R9 and R10; or R8, R9, and R10 can together result in the formation of a cyclic moiety.

  本发明涉及一种化合物，其结构式为：其中：R1为H、取代或未取代的烷基、羧酸酯或酰基；R2为H、OH、保护的羟基、取代或未取代的烷基、烯基、炔基、酰基、芳基或杂环芳基；R3为H、取代或未取代的烷基、羧酸酯或酰基；R8、R9和R10相同或不同且独立地选自以下组中的一种：H、取代或未取代的烷基、取代或未取代的芳基、取代或未取代的杂环芳基或卤素；且R8和R9、R8和R10、或R9和R10；或R8、R9和R10可以共同形成环状基团。
• PROCESS FOR PRODUCTION OF DELTA-9-TETRAHYDROCANNABINOL
  申请人：BURDICK David C.

  公开号：US20100069651A1

  公开（公告）日：2010-03-18

  The present invention relates to a process for preparation of a delta-9-tetrahydrocannabinol compound or derivative thereof involving treating a first intermediate compound with an organoaluminum-based Lewis acid catalyst, under conditions effective to produce the delta-9-tetrahydrocannabinol compound or derivative thereof. Another aspect of the present invention relates to a process for preparation of a cannabidiol or cannabidiolate compound involving reacting a first starting compound with a second starting compound in the presence of a metal triflate catalyst, under conditions effective to form the cannabidiol or cannabidiolate compound. The present invention also relates to a compound of the formula: where R 8 , R 9 , and R 10 are the same or different and independently selected from the group consisting of H, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or halo, with R 1 , R 2 , and R 3 defined herein.

  本发明涉及一种制备δ-9-四氢大麻酚化合物或其衍生物的过程，包括将第一中间化合物与基于有机铝的Lewis酸催化剂处理，在有效条件下产生δ-9-四氢大麻酚化合物或其衍生物。本发明的另一个方面涉及一种制备大麻二酚或大麻二酚盐化合物的过程，包括在金属三氟甲烷酸盐催化剂存在下，将第一起始化合物与第二起始化合物反应，在有效条件下形成大麻二酚或大麻二酚盐化合物。本发明还涉及一种化合物的公式：其中R8、R9和R10相同或不同，且独立地从H、取代或未取代的烷基、取代或未取代的芳基、取代或未取代的杂环芳基或卤素中选择，R1、R2和R3在此定义。