N-(2-hydroxy-5-nitrophenyl)formamide | 70886-35-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-(2-hydroxy-5-nitrophenyl)formamide
• 英文别名: 2-hydroxy-5-nitroformanilide
• CAS: 70886-35-0
• 化学式: C₇H₆N₂O₄
• 分子量: 182.136
• InChiKey: DBNAERXDKYYDSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  95.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2-hydroxy-5-nitrophenyl)formamide 生成 5-硝基-1,3-苯并噁唑
  参考文献：
  名称：

  一些杂环化合物的近紫外吸收光谱。第一部分苯并恶唑

  摘要：

  DOI：

  10.1039/jr9540002256
• 作为产物：
  描述：

  5-硝基-1,3-苯并噁唑 在 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以82%的产率得到N-(2-hydroxy-5-nitrophenyl)formamide
  参考文献：
  名称：

  硝基苯并恶唑中氢的取代亲核取代及相关反应

  摘要：

  5-和6-硝基苯并恶唑3和4仅在C-2处与亲核试剂反应，产生开环产物。如果2-位被苯基取代基封闭，则反应在碳环中发生，得到VNS产物。2-甲硫基-5-硝基苯并恶唑7及其-6-硝基异构体从添加的亲核试剂到碳环（VNS）的以及与杂环（S其导致8得到产物Ñ Ar和环切割）。2-甲基硫代苯并恶唑可以通过氧化水解容易地转化为相应的苯并恶唑酮。

  DOI：

  10.1016/0040-4020(95)00351-8

文献信息

• GLUCURONIDE PRODRUGS OF JANUS KINASE INHIBITORS
  申请人：THERAVANCE BIOPHARMA R&D IP, LLC

  公开号：US20180339990A1

  公开（公告）日：2018-11-29

  The invention relates to glucuronide prodrug compounds of Janus kinase (JAK) inhibitors having formula I: where W 1 , R 1 and A 1 are as defined. The invention also relates to pharmaceutical compositions comprising such compounds; methods of using such compounds to treat gastrointestinal inflammatory diseases; and processes and intermediates for preparing such compounds.

  本发明涉及具有公式I的糖苷酸前药化合物的Janus激酶（JAK）抑制剂：其中W1、R1和A1如所定义。本发明还涉及包含这些化合物的药物组合物；使用这些化合物治疗胃肠炎性疾病的方法；以及制备这些化合物的过程和中间体。
• [EN] GLUCURONIDE PRODRUGS OF TOFACITINIB<br/>[FR] PROMÉDICAMENTS À BASE DE GLUCURONIDE DE TOFACITINIB
  申请人：THERAVANCE BIOPHARMA R&D IP LLC

  公开号：WO2018165250A1

  公开（公告）日：2018-09-13

  The invention relates to glucuronide prodrug compounds of the Janus kinase (JAK) inhibitor tofacitinib having formula (I): (Formula (I)) where A1 and R1 are as defined. The invention also relates to pharmaceutical compositions comprising such compounds; methods of using such compounds to treat gastrointestinal inflammatory diseases; and processes and intermediates for preparing such compounds.

  这项发明涉及具有式(I)的Janus激酶（JAK）抑制剂托法替尼的葡萄糖醛酸酯前药化合物：（式(I)）其中A1和R1如所定义。该发明还涉及包含这种化合物的药物组合物；使用这种化合物治疗胃肠道炎症性疾病的方法；以及制备这种化合物的过程和中间体。
• Metal-free N-formylation of 2-aminophenols using dimethylformamide and CSA
  作者：Yuanyong Yang、Yingxian Li、Zhenhua Zhang、Yonglong Zhao、Wei Feng

  DOI：10.1080/00397911.2019.1584319

  日期：2019.4.18

  Abstract DMF has been proved to be an efficient formylation reagent for 2-aminophenols in the presence of (±) camphorsulfonic acid (CSA) in this work. CSA works as an acid catalyst and a neutralizer of dimethyl amine which is kicked off from DMF. Both electron-withdrawing and electron-donating groups are tolerated. More importantly, the product could be achieved in gram scale with the possibility of

  摘要 在这项工作中，DMF 已被证明是在 (±) 樟脑磺酸 (CSA) 存在下用于 2-氨基苯酚的有效甲酰化试剂。CSA 作为酸催化剂和从 DMF 中分离出来的二甲胺的中和剂。吸电子基团和给电子基团都是可以容忍的。更重要的是，该产品可以达到克级规模，并有可能进一步多样化为具有生物学意义的结构。图形概要
• Organic Compounds
  申请人：Barnes David

  公开号：US20080262050A1

  公开（公告）日：2008-10-23

  Compounds of the formula are inhibitors of protein tyrosine phosphatases (PTPases) and, thus, may be employed for the treatment of conditions mediated by PTPase activity. The compounds of the present invention may also be employed as inhibitors of other enzymes characterized with a phosphotyrosine binding region such as the SH2 domain. The compounds of formula (I) may be employed for prevention and/or treatment of insulin resistance associated with obesity, glucose intolerance, diabetes mellitus, hypertension and ischemic diseases of the large and small blood vessels, conditions that accompany type-2 diabetes, including hyperlipidemia, hypertriglyceridemia, atherosclerosis, vascular restenosis, irritable bowel syndrome, pancreatitis, adipose cell tumors and carcinomas such as liposarcoma, dyslipidemia, and other disorders where insulin resistance is indicated. In addition, the compounds of the present invention may be employed to treat and/or prevent cancer, osteoporosis, neurodegenerative and infectious diseases, and diseases involving inflammation and the immune system.

  式(I)的化合物是蛋白酪氨酸磷酸酶（PTPases）的抑制剂，因此可用于治疗由PTPase活性介导的疾病。本发明的化合物也可用作其他酶的抑制剂，这些酶具有磷酸酪氨酸结合区域，例如SH2结构域。式(I)的化合物可用于预防和/或治疗与肥胖、葡萄糖不耐症、糖尿病、高血压和大、小血管缺血性疾病相关的胰岛素抵抗。这些疾病包括2型糖尿病的伴随症状，如高脂血症、高三酰甘油血症、动脉粥样硬化、血管再狭窄、肠易激综合征、胰腺炎、脂肪细胞肿瘤和脂肪肉瘤等癌症，以及脂质代谢紊乱和其他胰岛素抵抗相关的疾病。此外，本发明的化合物可用于治疗和/或预防癌症、骨质疏松症、神经退行性和传染性疾病，以及涉及炎症和免疫系统的疾病。
• Organic compounds
  申请人：Novartis AG

  公开号：US07700633B2

  公开（公告）日：2010-04-20

  Compounds of the formula are inhibitors of protein tyrosine phosphatases (PTPases) and, thus, may be employed for the treatment of conditions mediated by PTPase activity. The compounds of the present invention may also be employed as inhibitors of other enzymes characterized with a phosphotyrosine binding region such as the SH2 domain. The compounds of formula (I) may be employed for prevention and/or treatment of insulin resistance associated with obesity, glucose intolerance, diabetes mellitus, hypertension and ischemic diseases of the large and small blood vessels, conditions that accompany type-2 diabetes, including hyperlipidemia, hypertriglyceridemia, atherosclerosis, vascular restenosis, irritable bowel syndrome, pancreatitis, adipose cell tumors and carcinomas such as liposarcoma, dyslipidemia, and other disorders where insulin resistance is indicated. In addition, the compounds of the present invention may be employed to treat and/or prevent cancer, osteoporosis, neurodegenerative and infectious diseases, and diseases involving inflammation and the immune system.

  公式为（I）的化合物是蛋白酪氨酸磷酸酶（PTPases）的抑制剂，因此可以用于治疗由PTPase活性介导的疾病。本发明的化合物也可以用作其他具有磷酸酪氨酸结合区域（如SH2结构域）特征的酶的抑制剂。公式（I）的化合物可用于预防和/或治疗与肥胖、葡萄糖不耐受、糖尿病、高血压和大、小血管缺血性疾病相关的胰岛素抵抗症，伴随2型糖尿病的病状，包括高脂血症、高三酰甘油血症、动脉粥样硬化、血管再狭窄、肠易激综合征、胰腺炎、脂肪细胞肿瘤和脂肪肉瘤癌等，以及其他显示胰岛素抵抗的疾病。此外，本发明的化合物还可用于治疗和/或预防癌症、骨质疏松症、神经退行性和传染性疾病，以及涉及炎症和免疫系统的疾病。

表征谱图