1,3-dihydro-7-iodo-5-phenyl-2H-1,4-benzodiazepine-2-thione | 97423-33-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: 1,3-dihydro-7-iodo-5-phenyl-2H-1,4-benzodiazepine-2-thione
• 英文别名: 7-iodo-5-phenyl-1,3-dihydro-2H-benzo[e][1,4]diazepine-2-thione；7-iodo-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepine-2-thione；7-iodo-5-phenyl-1,3-dihydro-1,4-benzodiazepine-2-thione
• CAS: 97423-33-1
• 化学式: C₁₅H₁₁IN₂S
• 分子量: 378.236
• InChiKey: XSYYNEJBVSBDTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  56.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3-dihydro-7-iodo-5-phenyl-2H-1,4-benzodiazepine-2-thione 在 hydrazine hydrate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 0.5h， 生成 8-iodo-1-methyl-6-phenyl-4H-benzo[f][1,2,4]triazolo[4,3-a][1,4]diazepine
  参考文献：
  名称：

  Dual HDAC–BRD4 inhibitors endowed with antitumor and antihyperalgesic activity

  摘要：

  组蛋白去乙酰化酶（HDAC）是调节乙酰化组蛋白浓度的酶，乙酰化组蛋白与BET（Bromodomain and Extracellular domain）蛋白的溴域（BRD）相互作用，影响转录活性。同时阻断这两个表观遗传学因子已在各种癌细胞系中显示出协同作用。本文报道了我们设计、合成和活性测试的新型双重抑制剂，通过向一些先前由我们开发的含苯二氮平核心的HDAC抑制剂添加甲基三唑基团而获得。Alphascreen FRET试验表明，这些化合物能够与BRD4-1和BRD4-2蛋白相互作用，对后者具有一定的选择性，而HDAC抑制性质则通过免疫沉淀试验测量。抗增殖活性在C26腺癌、SSMC2黑色素瘤和SHSY5Y神经母细胞瘤细胞上进行了测试。有趣的是，这两种化合物在小鼠剩余神经损伤（SNI）模型中具有抗高痛感作用。

  DOI：

  10.1007/s00044-022-02896-w
• 作为产物：
  描述：

  2-氨基-5-碘苯甲酮 在 tetraphosphorus decasulfide 、 氨 作用下， 以 吡啶 、 甲苯 为溶剂， 反应 9.25h， 生成 1,3-dihydro-7-iodo-5-phenyl-2H-1,4-benzodiazepine-2-thione
  参考文献：
  名称：

  1-(2-Aminoethyl)-6-aryl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepines with diuretic and natriuretic activity

  摘要：

  A series of 1-(2-amino-1-phenylethyl)-6-phenyl-4H- [1,2,4]triazolo[4,3-a][1,4]benzodiazepines was prepared and evaluated for diuretic activity. These compounds have diuretic and natriuretic activity but no kaliuretic activity when evaluated by oral administration to the conscious rat. The structure requirements for this activity are discussed. In particular it was found that the 2-aminoethyl side chain at C-1 with hydrogen or methyl substituents on the amino group was required for diuretic activity. A substituent at C-8 was also required; soft substituents such as methylthio and iodo at this position favored activity. Compounds with both phenyl and 2-pyridyl substituents at C-6 were active; substituents on the C-6 phenyl, however, reduced or eliminated the activity. Substituents other than phenyl at the 1-position of the 2-aminoethyl side chain were detrimental to activity; phenyl substitution at this position was required for activity when the substituent at C-8 was chloro but not when it was bromo.

  DOI：

  10.1021/jm00126a003

文献信息

• 1-Ethanamine-triazolo-benzodiazepines as diuretics
  申请人：The Upjohn Company

  公开号：US04514407A1

  公开（公告）日：1985-04-30

  Triazolo-benzodiazepine-1-ethanamines of the formulas ##STR1## where R, R.sub.1, R.sub.2, R.sub.3, R.sub.4 and Ring A are as defined in the specification, e.g., 8-chloro-N,N-dimethyl-.beta.,6-diphenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benz odiazepine-1-ethanamine, and pharmacologically acceptable salts thereof, have been found to have substantial diuretic, natriuretic, but little, if any, kaliuretic activity, which can be used alone, or concomittently with other diuretic drugs such as furosemide or hydrochlorothiazide and/or with antihypertensive agents such as propranolo, captopril, minoxidil, prazosin, guanadrel sulfate, whose actions are supplemented by the action of a diuretic drug.

  Triazolo-苯二氮卓-1-乙胺的分子式为##STR1##其中R、R.sub.1、R.sub.2、R.sub.3、R.sub.4和环A如规范中所定义，例如8-氯-N，N-二甲基-β，6-二苯基-4H-[1,2,4]三唑并[4,3-a][1,4]苯二氮卓-1-乙胺及其药理学上可接受的盐，已被发现具有显著的利尿、排钠作用，但几乎没有钾排泄作用，可单独使用，或与其他利尿药物如呋塞米或氢氯噻嗪以及/或抗高血压药物如普萘洛尔、卡普托普利、米诺地尔、普拉唑辛、瓜那德雷酸盐同时使用，其作用被利尿药物的作用所补充。
• Triazolo-benzodiazepine-1-ethanamines as diuretics
  申请人：The Upjohn Company

  公开号：US04689413A1

  公开（公告）日：1987-08-25

  Triazolo-benzodiazepine-1-ethanamines of the formulas ##STR1## where R, R.sub.1, R.sub.2, R.sub.3, R.sub.4 and Ring A are as defined in the specification, e.g., 8-chloro-N,N-dimethyl-.beta.,6-diphenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benz odiazepine-1-ethanamine, and pharmacologically acceptable salts thereof, have been found to have substantial diuretic, natriuretic, but little, if any, kaliuretic activity, which can be used alone, or concomittently with other diuretic drugs such as furosemide or hydrochlorothiazide and/or with antihypertensive agents such as propranolol, captopril, minoxidil, prazosin, guanadrel sulfate, whose actions are supplemented by the action of a diuretic drug.

  公式为##STR1##的Triazolo-benzodiazepine-1-ethanamines，其中R，R.sub.1，R.sub.2，R.sub.3，R.sub.4和环A的定义如规范中所述，例如8-氯-N，N-二甲基-β，6-二苯基-4H-[1，2，4]三唑[4，3-a][1,4]苯并二氮平-1-乙胺及其药理学上可接受的盐，已发现具有显著的利尿、钠利尿作用，但几乎没有钾利尿作用，可单独使用，或与其他利尿药物如呋塞米或氢氯噻嗪和/或降压药物如普萘洛尔、卡托普利、米诺地尔、普拉索辛、磺酸冠脲等同时使用，这些药物的作用通过利尿药物的作用得到补充。
• HESTER, JACKSON B. , JR.;LUDENS, JAMES H.
  作者：HESTER, JACKSON B. , JR.、LUDENS, JAMES H.

  DOI：——

  日期：——
• US4514407A
  申请人：——

  公开号：US4514407A

  公开（公告）日：1985-04-30
• US4689413A
  申请人：——

  公开号：US4689413A

  公开（公告）日：1987-08-25