3a,8a-dihydroxy-1,3-diphenyl-2-thioxo-2,3,3a,8a-tetrahydro-1H-indeno[1,2-d]imidazole-8-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 3a,8a-dihydroxy-1,3-diphenyl-2-thioxo-2,3,3a,8a-tetrahydro-1H-indeno[1,2-d]imidazole-8-one
• 英文别名: 3a,8a-dihydroxy-1,3-diphenyl-2-thioxo-2,3,3a,8a-tetrahydro-1H-indeno[1,2-d]imidazol-8-one；3a,8a-Dihydroxy-1,3-diphenyl-2-thioxo-2,3,3a,8a-tetrahydroindeno[1,2-d]imidazol-8(1H)-one；3a,8b-dihydroxy-1,3-diphenyl-2-sulfanylideneindeno[1,2-d]imidazol-4-one
• 化学式: C₂₂H₁₆N₂O₃S
• mdl: MFCD01926045
• 分子量: 388.447
• InChiKey: QZYDMWIHROOQLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  96.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  水合茚三酮 、 N,N'-二苯基硫脲 以 水 为溶剂， 反应 0.75h， 以95%的产率得到3a,8a-dihydroxy-1,3-diphenyl-2-thioxo-2,3,3a,8a-tetrahydro-1H-indeno[1,2-d]imidazole-8-one
  参考文献：
  名称：

  A Green Approach to Synthesize and in vitro Antimicrobial Activity of Indeno-Imidazole Derivatives and Ninhydrin-Nucleophile Adducts

  摘要：

  水合茚三酮（1）在H2O/EtOH介质中与弱氮亲核试剂（2a-2f）反应，生成了相应的吲哚并咪唑衍生物（3a-3d）和水合茚三酮-亲核试剂加合物（3e-3f）。通过UV、IR、1H NMR、13C NMR光谱以及元素分析确认了化合物（3a-3f）的结构。合成化合物通过Kirby-Bauer纸片扩散法评估了其抗菌活性，其中大多数化合物显示出较好至中等的抗菌活性。

  DOI：

  10.14233/ajchem.2016.19775

文献信息

• Synthesis, Antimicrobial and Cholinesterase Enzymes Inhibitory Activities of Indeno Imidazoles and X-Ray Crystal Structure of 3a,8a-Dihydroxy-1,3-diphenyl-1,3,3a,8a-tetrahydro-indeno[1,2-d]imidazole-2,8-dione
  作者：Raza Murad Ghalib、Rokiah Hashim、Solhe F. Alshahateet、Sayed Hasan Mehdi、Othman Sulaiman、Kit-Lam Chan、Vikneswaran Murugaiyah、Ali Jawad

  DOI：10.1007/s10870-012-0288-7

  日期：2012.8

  Two indeno imidazoles have been synthesized by the reaction of ninhydrin with diphenylurea and diphenylthiourea. The structures have been determined by spectral analysis. The supramolecular behavior of 3a,8a-Dihydroxy-1,3-diphenyl-1,3,3a,8a-tetrahydro-indeno[1,2-d]imidazole-2,8-dione (1) was thoroughly analyzed and reported using X-ray single crystal technique and concepts. The presence of oxygen and nitrogen atoms led to very interesting supramolecular motifs interactions such as nitrogen–oxygen, nitrogen–nitrogen, oxygen–oxygen, nitrogen–hydrogen, and oxygen–hydrogen. 3a,8a-dihydroxy-1,3-diphenyl-2-thioxo-2,3,3a,8a-tetrahydro-1H-indeno[1,2-d]imidazol-8-one 2 showed good antibacterial activity against B. subtilis and P. aeruginosa, while 3a,8a-dihydroxy-1,3-diphenyl-1,3,3a,8a-tetrahydro-indeno[1,2-d]imidazole-2,8-dione 1 only showed antibacterial activity against P. aeruginosa. Both of 1 and 2 were inactive against C. albicans. Derivative 2 demonstrated good cholinesterase enzyme activity unlike derivative 1 which has weak inhibitory activity against these enzymes. Furthermore, 2 was found to be a selective butyrylcholinesterase enzyme inhibitor that has potential use for prevention of further neurodegeneration as well for symptomatic treatment of Alzheimer patients. The non-covalent interactions involved in the crystal structure of 3a,8a-Dihydroxy-1,3-diphenyl-1,3,3a,8a-tetrahydro-indeno[1,2-d]imidazole-2,8-dione (1) were investigated and reported in terms of crystal engineering and supramolecular chemistry. Different motifs of N···H and O···H interactions as well as N···O, N···N, and O···O are adopted by the crystal structure and led to a strong crystal packing.

  通过茚三酮与二苯基脲和二苯基硫脲的反应，合成了两种茚并咪唑。通过光谱分析确定了它们的结构。利用 X 射线单晶技术和概念对 3a,8a-二羟基-1,3-二苯基-1,3,3a,8a-四氢-茚并[1,2-d]咪唑-2,8-二酮 (1) 的超分子行为进行了深入分析和报告。氧原子和氮原子的存在导致了非常有趣的超分子相互作用，如氮氧、氮氮、氧氧、氮氢和氧氢。3a,8a-二羟基-1,3-二苯基-2-硫酮-2,3,3a,8a-四氢-1H-茚并[1,2-d]咪唑-8-酮 2 对枯草杆菌和铜绿假单胞菌具有良好的抗菌活性，而 3a,8a而 3a,8a-二羟基-1,3-二苯基-1,3,3a,8a-四氢-茚并[1,2-d]咪唑-2,8-二酮 1 只对绿脓杆菌具有抗菌活性。1 和 2 对白僵菌均无活性。衍生物 2 具有良好的胆碱酯酶活性，而衍生物 1 对这些酶的抑制活性较弱。此外，研究还发现 2 是一种选择性丁酰胆碱酯酶抑制剂，具有防止神经进一步变性以及对阿尔茨海默氏症患者进行对症治疗的潜力。研究人员从晶体工程学和超分子化学的角度研究并报告了 3a,8a-二羟基-1,3-二苯基-1,3,3a,8a-四氢-茚并[1,2-d]咪唑-2,8-二酮（1）晶体结构中涉及的非共价相互作用。晶体结构采用了不同的 N--H、O--H 以及 N--O、N--N 和 O-O 相互作用模式，并形成了较强的晶体堆积。
• Quantitative Reaction Cascades of Ninhydrin in the Solid State
  作者：Gerd Kaupp、M. Reza Naimi-Jamal、Jens Schmeyers

  DOI：10.1002/1521-3765(20020201)8:3<594::aid-chem594>3.0.co;2-5

  日期：2002.2.1

  Crystalline ninhydrin (1) undergoes waste-free solid-state cascade reactions with dimedone, L-proline, three omicron-phenyienediamines, omicron-mercaptoaniline, two ureas, three thioureas, and methyl 3-aminocrotonate. The yields are quantitative and give pure crystalline products without workup just by milling stoichiometric mixtures of the crystalline reagents. The structures of the new and the previously obtained products with lower yields from solutions are established or confirmed by spectroscopic data and density functional calculations at the B3LYP/6-31G* level. The success of 3- and 4-cascade reactions in the crystal without melting is unusual and of unmatched atom economy. They are mechanistically investigated with atomic force microscopy techniques (AFM) on six different faces of 1 when omicron-phenylenediamine was the reagent (substitution, elimination, cyclization, elimination) and interpreted on the basis of known crystal structure data. Strict correlations to the crystal packings are observed. The characteristic surface features grow to mum heights in some cases at distances of 0.5 mm. from the contact edge of the reacting crystals. The waste-free and easy syntheses of highly functionalized (C=O; O-H, C=N) heterocycles or of a tetraketone are also of interest for synthetic use.
• Sarra; Stephani, Medicinal Chemistry Research, 2000, vol. 10, # 2, p. 81 - 91
  作者：Sarra、Stephani

  DOI：——

  日期：——
• A Green Approach to Synthesize and in vitro Antimicrobial Activity of Indeno-Imidazole Derivatives and Ninhydrin-Nucleophile Adducts
  作者：Samia Rifat、Khorshada Jahan、U.K.R. Romman、Kawsari Akhter、Md. Ershad Halim

  DOI：10.14233/ajchem.2016.19775

  日期：——

  Ninhydrin (1) reacted with weak nitrogen nucleophiles (2a-2f) in the presence of H2O/EtOH medium to give the corresponding indeno-imidazole derivatives (3a-3d) and ninhydrin-nucleophile adducts (3e-3f). The structures of the compounds (3a-3f) were confirmed by their UV, IR, 1H NMR, 13C NMR spectra and elemental analyses. The synthesized compounds were evaluated for their antimicrobial activity by Kirby-Bauer disk diffusion method. Most of the compounds showed good to moderate antimicrobial activity.

  水合茚三酮（1）在H2O/EtOH介质中与弱氮亲核试剂（2a-2f）反应，生成了相应的吲哚并咪唑衍生物（3a-3d）和水合茚三酮-亲核试剂加合物（3e-3f）。通过UV、IR、1H NMR、13C NMR光谱以及元素分析确认了化合物（3a-3f）的结构。合成化合物通过Kirby-Bauer纸片扩散法评估了其抗菌活性，其中大多数化合物显示出较好至中等的抗菌活性。