4-amino-3-mercapto-5-[1-(tricyclo[3.3.1.1^3,7]decane)]-4(H)-1,2,4-triazole | 151017-99-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-amino-3-mercapto-5-[1-(tricyclo[3.3.1.1^3,7]decane)]-4(H)-1,2,4-triazole
• 英文别名: 5-(1-adamantyl)-4-amino-4H-1,2,4-triazol-3-thiol；3-(1-adamantyl)-4-amino-5-mercapto-1,2,4-thiazole；5-(1-adamantyl)-4-amino-3-mercapto-1,2,4-triazole；3-(1-adamantyl)-4-amino-4,5-dihydro-1H-1,2,4-triazole-5-thione；3-(1-adamantyl)-4-amino-1H-1,2,4-triazole-5-thione
• CAS: 151017-99-1
• 化学式: C₁₂H₁₈N₄S
• 分子量: 250.368
• InChiKey: SBMKCHWGSHDOJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.833
• 拓扑面积：
  85.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-amino-3-mercapto-5-[1-(tricyclo[3.3.1.1^3,7]decane)]-4(H)-1,2,4-triazole 以 乙醇 为溶剂， 反应 12.25h， 生成 5-(1-adamantyl)-4-[(E)-(2-hydroxyphenyl)methylideneamino]-2-[[4-(2-methoxyphenyl)piperazin-1-yl]methyl]-1,2,4-triazole-3-thione
  参考文献：
  名称：

  Synthesis and antimicrobial activity of novel 5-(1-adamantyl)-2-aminomethyl-4-substituted-1,2,4-triazoline-3-thiones

  摘要：

  The reaction of 5-(1-adamantyl)-4-substituted-1,2,4-triazoline-3-thione 5a,b and 10a,b with formaldehyde solution and various primary aromatic amines or 1-substituted piperazines yielded the corresponding N-Mannich bases 6a-o, 7a-g and 11a-i. The newly synthesized N-Mannich bases 6a-o, 7a-o and 11a-i were tested for in vitro inhibitory activities against a panel of Gram-positive and Gram-negative bacteria and the yeast-like pathogenic fungus Candida albicans. The compounds 6j, 6l, 6m, 7a, 7b, 7c, 7d, 7f, 11a, 11b, 11c, 11d, lie, 11f, 11h and 11i displayed moderate to good activity against the tested Gram-positive bacteria, while compounds 7c,11c,11d,11f and 11h showed potent broad spectrum antibacterial activity. None of the newly synthesized compounds were proved to possess marked activity against C albicans. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.07.024
• 作为产物：
  描述：

  金刚烷-1-甲酰肼 在 potassium hydroxide 、 肼 作用下， 以 乙醇 为溶剂， 生成 4-amino-3-mercapto-5-[1-(tricyclo[3.3.1.1^3,7]decane)]-4(H)-1,2,4-triazole
  参考文献：
  名称：

  Synthesis and antimicrobial activity of novel 5-(1-adamantyl)-2-aminomethyl-4-substituted-1,2,4-triazoline-3-thiones

  摘要：

  The reaction of 5-(1-adamantyl)-4-substituted-1,2,4-triazoline-3-thione 5a,b and 10a,b with formaldehyde solution and various primary aromatic amines or 1-substituted piperazines yielded the corresponding N-Mannich bases 6a-o, 7a-g and 11a-i. The newly synthesized N-Mannich bases 6a-o, 7a-o and 11a-i were tested for in vitro inhibitory activities against a panel of Gram-positive and Gram-negative bacteria and the yeast-like pathogenic fungus Candida albicans. The compounds 6j, 6l, 6m, 7a, 7b, 7c, 7d, 7f, 11a, 11b, 11c, 11d, lie, 11f, 11h and 11i displayed moderate to good activity against the tested Gram-positive bacteria, while compounds 7c,11c,11d,11f and 11h showed potent broad spectrum antibacterial activity. None of the newly synthesized compounds were proved to possess marked activity against C albicans. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.07.024

文献信息

• Microwave-Assisted Dehydrosulfurization: An Efficient, Solvent-Free Synthesis of 5-(1-Adamantyl)-2-arylamino-1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles
  作者：Ali A. El-Emam、Ebtehal S. Al-Abdullah、Ihsan A. Shehata、Omar A. Al-Deeb

  DOI：10.3987/com-06-10906

  日期：——

  A fast and efficient microwave-assisted synthesis of 2-arylamino-5-(1-adamantyl)-1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles is described. The reaction of 3-(l-adamantyl)-5-mercapto-l,2,4-triazole (2) with arylisothiocyanates in DMF at room temperature yielded the corresponding N,N'-disubstituted thioureas (3a-e) in high yields. Compounds (3a-e) were desulfurized via microwave irradiation for 5 min to

  描述了一种快速高效的微波辅助合成 2-arylamino-5-(1-adamantyl)-1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles。3-(l-金刚烷基)-5-巯基-l,2,4-三唑 (2) 与芳基异硫氰酸酯在 DMF 中在室温下以高产率反应生成相应的 N,N'-二取代硫脲 (3a-e) . 化合物(3a-e)通过微波辐射脱硫5分钟，得到相应的5-(l-金刚烷基)-2-芳氨基-1,2,4-三唑并[3,4-b][1,3,4 ]噻二唑（4a-e）。化合物(4a-e)也通过微波辐射(2)和相应的芳基异硫氰酸酯的混合物8分钟以高产率制备。尝试通过微波辐射制备脂肪族类似物 (6a-e) 未成功，通过在 DMF 中将化合物 (2) 与相应的脂肪族异硫氰酸酯长时间加热，它们的收率很低。化合物(6a-e)通过(2)与溴化氰反应产生2-氨基类似物(7)，其随后与相应的脂肪族卤化物反应以良好的产率独立获得。
• Synthesis, Antimicrobial, and Anti-inflammatory Activities of Novel 5-(1-Adamantyl)-4-arylideneamino-3-mercapto-1,2,4-triazoles and Related Derivatives
  作者：Mohamed A. Al-Omar、Ebtehal S. Al-Abdullah、Ihsan A. Shehata、Elsayed E. Habib、Tarek M. Ibrahim、Ali A. El-Emam

  DOI：10.3390/molecules15042526

  日期：——

  The reaction of 5-(1-adamantyl)-4-amino-3-mercapto-1,2,4-triazole (5) with various aromatic aldehydes in ethanol or acetic acid yielded the corresponding 4-arylideneamino derivatives 6a-v. Treatment of the 4-(2,6-difluoro- and dichlorobenzylideneamino) derivatives 6o and 6q with 1-substituted piperazines, and formaldehyde solution in ethanol afforded good yields of the corresponding 5-(1-adamantyl)-4-(2

  5-(1-金刚烷基)-4-氨基-3-巯基-1,2,4-三唑 (5) 与各种芳香醛在乙醇或乙酸中的反应产生相应的 4-亚芳基氨基衍生物 6a-v。4-(2,6-二氟-和二氯亚苄基氨基)衍生物 6o 和 6q 用 1-取代哌嗪和甲醛的乙醇溶液处理得到相应的 5-(1-金刚烷基)-4-(2,6 -dihalobenzylideneamino-2-(4-located-1-piperazinylmethyl)-1,2,4-triazoline-3-thiones 7a-p.5-(1-Adamantyl)-4-arylideneamino-2-(4-ethoxycarbonyl-1) -哌啶基甲基)-1,2,4-三唑啉-3-硫酮8a-n，通过相应的亚芳基氨基衍生物与4-哌啶羧酸乙酯和甲醛在乙醇中的溶液的反应类似地制备。化合物6a-v，测试了 7a-p 和 8a-n 对一组革兰氏阳性和革兰氏阴性细菌以
• 11-Beta-hydroxysteroid dehydrogenase 1 inhibitors useful for the treatment of diabetes, obesity and dyslipidemia
  申请人：Balkovec M. James

  公开号：US20050070720A1

  公开（公告）日：2005-03-31

  Compounds having Formula (I), including pharmaceutically acceptable salts and prodrugs thereof: are selective inhibitors of the 11β-HSD1 enzyme. They inhibit the 11β-HSD1-mediated conversion of cortisone and other 11-keto-glucocorticoids to cortisol and other 11β-hydroxy-glucocorticoids. The 11β-HSD1 inhibitors therefore decrease the amount of cortisol in target tissues, thereby modulating the effects of cortisol. Modulation of cortisol may be effective in controlling non-insulin-dependent diabetes (NIDDM), hyperglycemia, obesity, insulin resistance, dyslipidemia, hyperlipidemia, hypertension, Syndrome X, and other symptoms associated with NIDDM or with excess cortisol in the body.

  化合物公式为（I）的化合物，包括其药学上可接受的盐和前药：是11β-HSD1酶的选择性抑制剂。它们抑制11β-HSD1介导的可的松和其他11-酮基-糖皮质激素转化为皮质醇和其他11β-羟基-糖皮质激素的过程。因此，11β-HSD1抑制剂减少了目标组织中皮质醇的含量，从而调节了皮质醇的效应。调节皮质醇可能对控制非胰岛素依赖性糖尿病（NIDDM）、高血糖、肥胖症、胰岛素抵抗、血脂异常、高脂血症、高血压、X综合征和与体内过多皮质醇有关的其他症状有效。
• Marakos, Panagiotis; Papakonstantinou-Garoufalias, Spyroula; Tani, Ekaterini, Arzneimittel-Forschung/Drug Research, 2002, vol. 52, # 7, p. 572 - 577
  作者：Marakos, Panagiotis、Papakonstantinou-Garoufalias, Spyroula、Tani, Ekaterini、Kourounakis, Panos N.、Athanasiou, George、Chytyroglou-Lada, Aikaterini

  DOI：——

  日期：——
• Al-Deeb, Omar A.; Al-Omar, Mohamed A.; El-Brollosy, Nasser R., Arzneimittel-Forschung/Drug Research, 2006, vol. 56, # 1, p. 40 - 47
  作者：Al-Deeb, Omar A.、Al-Omar, Mohamed A.、El-Brollosy, Nasser R.、Habib, Elsayed E.、Ibrahim, Tarek M.、El-Emam, Ali A.

  DOI：——

  日期：——