[(2,4-Diphenyl-3-azabicyclo[3.3.1]nonan-9-ylidene)amino]thiourea | 1148058-58-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: [(2,4-Diphenyl-3-azabicyclo[3.3.1]nonan-9-ylidene)amino]thiourea
• CAS: 1148058-58-5
• 化学式: C₂₁H₂₄N₄S
• 分子量: 364.514
• InChiKey: FZBXSVPFDCIYND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  94.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [(2,4-Diphenyl-3-azabicyclo[3.3.1]nonan-9-ylidene)amino]thiourea 、 丁炔二酸二甲酯 在 丁炔二酸二乙酯 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以81%的产率得到methyl 2-(2-(2,4-diphenyl-3-azabicyclo[3.3.1]nonan-9-ylidene)hydrazinyl)-4-oxo-4H-1,3-thiazine-6-carboxylate
  参考文献：
  名称：

  一些新型噻嗪酮和缩氨基硫脲衍生物的合成、表征和抗肿瘤活性

  摘要：

  摘要 使用 2,4-二芳基-3-氮杂双环[3.3.1]壬烷-9-酮 (ABNs) 和 3-烷基-2,6-二芳基哌啶-4 合成了两个系列的噻嗪酮和缩氨基硫脲衍生物 (1-12) ——作为起始材料。新合成化合物的结构是在红外光谱、核磁共振光谱和质谱的基础上建立的。从光谱数据中，我们确定硫代酰胺与乙炔二羧酸二烷基酯的环化反应选择性地得到六元甲基 2-(2-(2,4-二取代-3-氮杂双环 [3.3.1]nonan-9-ylidene)hydrazinyl)- 4-oxo-4H-1,3-thiazine-6-carboxylates (1-6)。为了研究合成化合物的抗肿瘤活性，使用人前列腺癌细胞系进行了体外细胞毒性研究。测试的化合物对癌细胞系显示出良好/中等的活性，并通过活/死测定进行了进一步研究。图形概要

  DOI：

  10.1080/10426507.2020.1757672
• 作为产物：
  描述：

  环己酮 在 盐酸 、 ammonium acetate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 [(2,4-Diphenyl-3-azabicyclo[3.3.1]nonan-9-ylidene)amino]thiourea
  参考文献：
  名称：

  N-acetyl-2,4-[diaryl-3-azabicyclo[3.3.1]nonan-9-yl]-9-spiro-4'-acetyl-2'-(乙酰氨基）-4',9-二氢-[1',3',4']-噻二唑：一种潜在的 SARS-nCoV-2 Mpro (COVID-19) 抑制剂

  摘要：

  在本文中，我们描述了 N-acetyl-2,4-[diphenyl-3-azabicyclo[3.3.1]nonan-9-yl]-9-spiro-4'-acetyl-2' 的合成和晶体结构分析。 -(乙酰氨基)-4',9-二氢-[1',3',4']-噻二唑( 3a)和N-乙酰基-2,4-[双(对甲氧基苯基)-3-氮杂双环[3.3. 1]壬-9-基]-9-螺-4'-乙酰基-2'-(乙酰氨基)-4',9-二氢-[1',3',4']-噻二唑(3b )。标题化合物3a和3b通过 1D NMR 和单晶 X 射线衍射分析进行了表征。分子中的非共价相互作用通过 Hirshfeld 表面（d范数接触和 2D 指纹图）分析来确定。此外，分子结构中存在硫族键（S•••O 键）（3a和3b ) 用 NCI-RDG 和 QTAIM 分析进行描述。NBO 分析用于描述硫和氧原子之间的轨道相互作用和电子转移。对化合物3a和3b与

  DOI：

  10.1016/j.molstruc.2022.132747

文献信息

• Efficient synthesis, spectral analysis and antimicrobial studies of nitrogen and sulfur containing spiro heterocycles from 2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ones
  作者：M. Rani、R. Ramachandran、S. Kabilan

  DOI：10.1016/j.bmcl.2010.09.021

  日期：2010.11

  cyclization of 2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-one thiosemicarbazones (2a–2h, 3a and 3b) with acetic anhydride/propionic anhydride and were characterized by Elemental analysis, IR, 1H NMR and 13C NMR spectral analysis. Single crystal X-ray diffraction has also been recorded for compounds 4c and 5a. From the NMR and Single crystal X-ray diffraction analysis, compounds 4b–4d, 4f–4h, 5b, 5c, 5f–5h, 6a

  乙酰基和丙酰基取代的噻二唑衍生物（4a - 4h，5a - 5h，6a，6b，7a和7b）是通过2，4-二芳基-3-氮杂双环[3.3.1] nonan-9-one的环化反应合成的硫代半氨基甲酮（2a – 2h，3a和3b）与乙酸酐/丙酸酐的混合物，并通过元素分析，IR，1 H NMR和13 C NMR光谱进行了表征。还记录了化合物4c和5a的单晶X射线衍射。通过NMR和单晶X射线衍射分析，发现化合物4b - 4d，4f - 4h，5b，5c，5f - 5h，6a，7a和7b采用双椅构型，而化合物4a，4e，5a，5d，5e和6b分别采用环己烷和哌啶环的椅子和船形。此外，使用系列稀释法筛选合成的化合物的抗菌和抗真菌活性。微生物学分析表明，基于氮杂双环壬烷的噻二唑4c / 4h和5c / 5h的C-2和C-4的吸电子功能取代了苯基，对伤寒沙门氏菌，大肠杆菌，肺炎克雷伯菌，黄曲霉，黑曲霉具有显着的抗菌活性。和白色念珠菌的MIC为6
• Design, synthesis and biological evaluation of novel 2-[(2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ylidene)hydrazono]-1,3-thiazolidin-4-ones as a new class of antimicrobial agents
  作者：R. Ramachandran、M. Rani、S. Kabilan

  DOI：10.1016/j.bmcl.2009.03.093

  日期：2009.5

  New series of 2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-one thiosemicarbazones (9-16) obtained from the corresponding 2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ones (1-8) upon cyclization with ethylbromoacetate in the presence of sodium acetate-acetic acid buffer afforded novel 2-[(2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ylidene) hydrazono]-1,3-thiazolidin-4-ones (17-24). The synthesized compounds have been characterized by their elemental, analytical and spectral studies. Besides, the reported compounds were screened for their antibacterial and antifungal activities against a spectrum of microbial organisms. These studies proved that compounds 11/18/20/23 against Staphylococcus aureus, 19/20/24 against Salmonella typhi show maximum inhibition potency at low concentration (6.25 mu g/ml) whereas 18/19 against Candida albicans and 19/20/21 against Rhizopus sp. showed beneficial antifungal activity at minimum concentration. (C) 2009 Elsevier Ltd. All rights reserved.
• Efficient Synthesis of Novel 2,4-[Diaryl-3-azabicyclo[3.3.1]nonan-9-yl]-5-spiro-4-acetyl-2-(acetylamino)-<font>Δ</font> ²-1,3,4-thiadiazolines
  作者：M. Rani、R. Ramachandran、S. Kabilan

  DOI：10.1080/00397910903161694

  日期：2010.5.11

  2,4-[Diaryl-3-azabicyclo[3.3.1]nonan-9-yl]-5-spiro-4-acetyl-2-(acetylamino)-2-1,3,4-thiadiazoline derivatives (3a-h) have been synthesized by the cyclization of 2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-one thiosemicarbazones (2a-h) under acetylating condition. The synthesized compounds were characterized by analytical and spectral (infrared, 1H NMR, and 13C NMR) studies.
• Synthesis, structure and conformational analysis of 2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-one thiosemicarbazones and semicarbazones
  作者：R. Ramachandran、M. Rani、S. Kabilan

  DOI：10.1016/j.molstruc.2010.02.005

  日期：2010.4

  A series of thiosemicarbazones and semicarbazones have been synthesized and characterized by one and two dimensional NMR spectroscopy. The possible ring conformations of both the hydrazones are discussed. The chemical shifts and coupling constants suggest that the reported hydrazones adopt twin-chair conformations with equatorial orientation of the aryl substituents. Besides, the proposed conformations are further confirmed by single crystal X-ray diffraction analysis and molecular optimization geometry method. Crown Copyright (C) 2010 Published by Elsevier B.V. All rights reserved.