8-硝基-2,3,4,5-四氢-1H-苯并[c]氮杂卓 | 223915-75-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 中文名称: 8-硝基-2,3,4,5-四氢-1H-苯并[c]氮杂卓
• 中文别名: 8-硝基-2,3,4,5-四氢-1H-苯并[C]氮杂卓
• 英文名称: 8-nitro-2,3,4,5-tetrahydro-1H-2-benzazepine
• 英文别名: 8-Nitro-2,3,4,5-tetrahydro-1H-benzo[c]azepine
• CAS: 223915-75-1
• 化学式: C₁₀H₁₂N₂O₂
• 分子量: 192.217
• InChiKey: SMAZDNVHMACXLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  8-硝基-2,3,4,5-四氢-1H-苯并[c]氮杂卓 在 platinum(IV) oxide 4-二甲氨基吡啶 、 正丁基锂 、 三氟过氧乙酸 、 氢溴酸 、 氢气 、 亚硝酸 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 、 水 、 三氟乙酸 为溶剂， -78.0~80.0 ℃ 、344.74 kPa 条件下， 反应 52.5h， 生成 8-methylsulfonyl-2,3,4,5-tetrahydro-1H-2-benzazepine
  参考文献：
  名称：

  Effects of a 3-Alkyl-, 4-Hydroxy- and/or 8-Aromatic-substituent on the Phenylethanolamine N-Methyltransferase Inhibitor Potency and α2-Adrenoceptor Affinity of 2,3,4,5-Tetrahydro-1H-2-benzazepines

  摘要：

  2,3,4,5-Tetrahydro-1H-2-benzazepine (THBA; 1) is nearly 100-fold more selective an inhibitor of phenylethanolamine N-methyltransferase (PNMT, EC 2.1.1.28) versus the alpha (2)-adrenoceptor than is 1,2,3,4-tetrahydroisoquinoline (THIQ; 2) (1: PNMT K-i = 3.3 muM, alpha (2)-adrenoceptor K-i = 11 muM, selectivity [alpha (2) K-i/PNMT K-i = 3.3; 2: PNMT K-i = 9.7 muM, alpha (2) K-i = 0.35 muM, selectivity 0.036;). Since the PNMT inhibitory activity and selectivity of THIQ were enhanced by the introduction of a hydrophilic electron-withdrawing 7-substituent and a 3-alkyl-substituent, a similar study was conducted on THBA. 8-Nitro-THBA (3) was found to be as potent an inhibitor of PNMT as its THIQ analogue (21) and to be more selective due to its reduced alpha (2)-adrenoceptor affinity (3: PNMT K-i = 0.39 muM, alpha (2) K-i = 66 muM, selectivity = 170; 21: PNMT K-i = 0.41 muM, (alpha (2) K-i = 4.3 muM, selectivity = 10). Introduction of a 3-alkyl substituent on the THBA nucleus decreased both the alpha (2)-adrenoceptor affinity and the PNMT inhibitory activity, suggesting an area of steric bulk intolerance at both sites. 4-Hydroxy-THBA (15), which can be considered a conformationally-restricted analogue of 3-hydroxymethyl-THIQ (30), exhibited poorer PNMT inhibitory activity and less selectivity than 30 (15: PNMT K-i = 58 muM, alpha (2) K-i = 100 muM, selectivity = 1.7; 30 PNMT K-i = 1.1 muM, alpha (2) K-i = 6.6 muM, selectivity = 6.0). While the addition of an 8-nitro group to 15 increased the selectivity of 16 as compared to its THIQ analogue (31), it was not as potent at PNMT nor as selective as 8-nitro-THBA (3) (16, PNMT K-i = 5.3 muM, alpha (2) K-i = 680 muM, selectivity = 130; 31: PNMT K-i = 0.29 muM, alpha (2) K-i = 19 muM, selectivity = 66). Compound 3 is the most selective (PNMT/alpha (2) and one of the more potent at PNMT compounds yet reported in the benzazepine series, and should have sufficient lipophilicity to penetrate the blood-brain barrier (CLogP = 1.8). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00112-2
• 作为产物：
  描述：

  8-nitro-1,3,4,5-tetrahydro-2H-2-benzazepine-2-carbaldehyde 在 sodium chloride 、 硫酸 作用下， 以 甲醇 为溶剂， 生成 8-硝基-2,3,4,5-四氢-1H-苯并[c]氮杂卓
  参考文献：
  名称：

  EP1122252

  摘要：

  公开号：

文献信息

• [EN] 2-SULFONYLAMINO-4-HETEROARYL BUTYRAMIDE ANTAGONISTS OF CCR10<br/>[FR] ANTAGONISTES DE 2-SULFONYLAMINO-4-HÉTÉROARYL BUTYRAMIDE DE CCR10
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2009126675A1

  公开（公告）日：2009-10-15

  This invention relates to a compound of formula (I) and the pharmaceutically acceptable salts thereof wherein R1, R2, R4. Ar and Het are as defined herein. The invention also relates to methods of using the compound of formula (I) to treat a diseases and disorders that are mediated or sustained through the activity of CCR10.

  本发明涉及一种具有式（I）的化合物及其药学上可接受的盐，其中R1、R2、R4、Ar和Het如本文中所定义。该发明还涉及使用式（I）的化合物治疗通过CCR10活性介导或维持的疾病和紊乱的方法。
• 1-Benzazepine-3-Sulfonylamino-2-Pyrroridones as Factor Xa Inhibitors
  申请人：Camus Laure

  公开号：US20080306045A1

  公开（公告）日：2008-12-11

  The invention relates to chemical entities of formula (I): and/or pharmaceutically acceptable derivative(s) thereof. The invention also relates to processes for the preparation of compounds of formula (I), pharmaceutical compositions containing compounds of formula (I) and to the use of compounds of formula (I) in medicine, particularly in the amelioration of a clinical condition for which a Factor Xa inhibitor is indicated.

  该发明涉及式(I)的化学实体和/或其药用可接受衍生物。该发明还涉及制备式(I)化合物的方法，含有式(I)化合物的药物组合物以及在医学中使用式(I)化合物，特别是在改善适用于Xa因子抑制剂的临床病况中的使用。
• Novel benzazepines and related heterocyclic derivatives which are useful as orexin receptor antagonists
  申请人：——

  公开号：US20040058912A1

  公开（公告）日：2004-03-25

  The invention relates to novel benzazepines and related heterocyclic derivatives (I) and their use as active ingredients in the preparation of pharmaceutical compositions. The invention also concerns related aspects including processes for the preparation of the compounds, pharmaceutical compositions containing one or more of those compounds and especially their use as orexin receptor antagonists.

  该发明涉及新型苯并吡嗪和相关杂环衍生物（I），以及它们作为药物组成物中的活性成分的用途。该发明还涉及相关方面，包括用于制备这些化合物的过程、含有这些化合物中的一个或多个的药物组成物，特别是它们作为促进睡眠的受体拮抗剂的用途。
• Amidine and isothiourea derivatives as inhibitors of nitric oxide
  申请人：Astra Aktiebolag

  公开号：US06140322A1

  公开（公告）日：2000-10-31

  There are provided novel compounds of formula (I) ##STR1## wherein X, R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are as defined in the specification and optical isomers and racemates thereof and pharmaceutically acceptable salts thereof; together with processes for their preparation, compositions containing them and their use in therapy.

  提供了式(I)的新化合物：##STR1## 其中X，R.sup.1，R.sup.2，R.sup.3，R.sup.4和R.sup.5如规范中所定义，以及其光学异构体和外消旋体以及其药学上可接受的盐；以及它们的制备过程，含有它们的组合物以及它们在治疗中的用途。
• Amidine and isothiourea derivatives, compositions containing them and
  申请人：Astra Aktiebolag

  公开号：US05929085A1

  公开（公告）日：1999-07-27

  There are provided novel compounds of formula (I) ##STR1## wherein X, R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are as defined in the specification and optical isomers and racemates thereof and pharmaceutically acceptable salts thereof; together with processes for their preparation, compositions containing them and their use in therapy.

  提供了式(I)的新化合物，其中X，R.sup.1，R.sup.2，R.sup.3，R.sup.4和R.sup.5如规范中所定义，以及其光学异构体和外消旋体以及其药学上可接受的盐;以及其制备过程，含有它们的组合物以及它们在治疗中的应用。