(4S)-4-phenylimidazolidine-2-thione | 16595-77-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4S)-4-phenylimidazolidine-2-thione
• CAS: 16595-77-0
• 化学式: C₉H₁₀N₂S
• 分子量: 178.258
• InChiKey: MABUPVNEGYIKOI-MRVPVSSYSA-N

物化性质

• 沸点：
  292.2±43.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  56.2
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (4S)-4-phenylimidazolidine-2-thione 生成 盐酸左旋咪唑
  参考文献：
  名称：

  THIJSSEN J. B. A.; KNAEPS A. G.; VERLUYTEN W. L. M.; HEYKANTS J. J. P.; J+, J. LABELLED COMPOUNDS AND RADIOPHARM., 24,(1987) N 7, 779-786

  摘要：

  DOI：
• 作为产物：
  描述：

  (R)-(-)-2-氯-1-苯乙醇 在 palladium on activated charcoal sodium hydroxide 、 sodium azide 、 偶氮二甲酸二异丙酯 、 氢气 、 焦磷酸硫胺素 、 肼 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 80.0 ℃ 、101.33 kPa 条件下， 反应 22.25h， 生成 (4S)-4-phenylimidazolidine-2-thione
  参考文献：
  名称：

  Enantioselective catalytic reductions of ketones with new four membered oxazaborolidines: Application to (S)-tetramisole

  摘要：

  Enantioselective catalytic reduction of ketones with both the enantiomers of new four membered oxazaborolidines is described.

  DOI：

  10.1016/s0957-4166(00)82184-9

文献信息

• Enantioselective Metal-Free Diamination of Styrenes
  作者：Caren Röben、José A. Souto、Yolanda González、Anton Lishchynskyi、Kilian Muñiz

  DOI：10.1002/anie.201103077

  日期：2011.9.26

  Metal‐free and asymmetric: The first enantioselective diamination of styrenes simply requires a chiral hypervalent iodine(III) reagent as an oxidant and bismesylimide as a nitrogen source (see scheme, Ms=methanesulfonyl). The reaction proceeds under mild conditions and with high enantiomeric excess.

  无金属且不对称：苯乙烯的第一次对映选择性胺化仅需要手性高价碘（III）试剂作为氧化剂，并使用双甲酰亚胺作为氮源（参见方案，Ms =甲磺酰基）。反应在温和条件下和高对映体过量下进行。
• Oxazoline-Based Organocatalyst for Enantioselective Strecker Reactions: A Protocol for the Synthesis of Levamisole
  作者：Arghya Sadhukhan、Debashis Sahu、Bishwajit Ganguly、Noor-ul H. Khan、Rukhsana I. Kureshy、Sayed H. R. Abdi、E. Suresh、Hari C. Bajaj

  DOI：10.1002/chem.201302007

  日期：2013.10.11

  catalyze asymmetric Strecker reactions of various aromatic and aliphatic N‐benzhydrylimines with trimethylsilyl cyanide (TMSCN) as a cyanide source at −20 °C to give α‐aminonitriles in high yield (96 %) with excellent chiral induction (up to 98 % ee). DFT calculations have been performed to rationalize the enantioselective formation of the product with the organocatalyst in these reactions. The organocatalyst

  已发现基于手性恶唑啉的有机催化剂可在-20°C下有效催化各种芳族和脂族N-苯甲酰肼与三甲基甲硅烷基氰化物（TMSCN）作为氰化物源的不对称Strecker反应，从而以高收率（96％）产生α-氨基腈具有出色的手性诱导作用（高达98％  ee）。在这些反应中，已经进行了DFT计算以使产物与有机催化剂的对映选择性形成合理化。有机催化剂已通过单晶X射线衍射分析以及其他分析方法进行了表征。该方案已扩展到以高收率和高对映选择性合成药学上重要的药物分子左旋咪唑。
• Immunostimulating 6-aryl-5,6-dihydroimidazo[2,1-b]thiazole derivatives
  申请人：JANSSEN PHARMACEUTICA N.V.

  公开号：EP0430334A1

  公开（公告）日：1991-06-05

  Novel 6-aryl-5,6-dihydroimidazo[2,1-b]thiazole derivatives of formula wherein Ar is phenyl optionally substituted with halo, hydroxy, C₁₋₆alkyloxy, mercapto, C₁₋₆alkylthio, C₁₋₆alkyl, nitro, amino, mono- and di(C₁₋₆alkyl)amino, C₁₋₆alkylcarbonylamino, arylcarbonylamino, C₁₋₆alkylsulfonylamino, trifluoromethyl, cyano, aminocarbonyl, mono- and di(C₁₋₆alkyl)aminocarbonyl, hydroxycarbonyl, C₁₋₆alkyloxycarbonyl, carboxaldehyde or hydroxymethyl; pyridinyl; thienyl; furanyl or furanyl substituted with either C₁₋₆alkyl or halo; R¹ and R² are C₁₋₂₀alkyl, (C₃₋₇cycloalkyl)C₁₋₆alkyl, C₃₋₇cycloalkyl, aryl or (aryl)C₁₋₆alkyl; one of R¹ and R² may by hydrogen; or R¹ and R² taken together may form a C₃₋₆alkanediyl radical; the acid addition salts and stereochemically isomeric forms thereof, said compounds having immunostimulating properties. Pharmaceutical compositions containing such compounds as active ingredient. Processes of preparing said novel compounds and pharmaceutical compositions.

  式中的新型 6-芳基-5,6-二氢咪唑并[2,1-b]噻唑衍生物 其中 Ar 是苯基，可任选被卤代、羟基、C₁₋₆alkyloxy、巯基、C₁₋₆alkylthio、C₁₋₆alkyl、硝基、氨基、单和双(C₁₋₆alkyl)氨基、C₁₋₆alkylcarbonylamino芳羰基氨基、C₁₋₆烷基磺酰基氨基、三氟甲基、氰基、氨基羰基、单和双（C₁₋₆烷基）氨基羰基、羟基羰基、C₁₋₆烷氧基羰基、羧基或羟甲基；吡啶基；噻吩基；呋喃基或被 C₁₋₆烷基或卤素取代的呋喃基； R¹和R²是C₁₋₂₀烷基、(C₃₋₇cyclo)C₁₋₆烷基、C₃₋₇cyclo烷基、芳基或(芳基)C₁₋₆烷基；R¹和R²中的一个可以是氢；或者R¹和R²合在一起可以形成C₃₋₆烷二基； 酸加成盐及其立体异构体，所述化合物具有免疫刺激特性。含有此类化合物作为活性成分的药物组合物。制备上述新型化合物和药物组合物的工艺。
• Potent and Selective Inhibitors of Histone Deacetylase-3 Containing Chiral Oxazoline Capping Groups and a <i>N</i>-(2-Aminophenyl)-benzamide Binding Unit
  作者：Charles M. Marson、Christopher J. Matthews、Stephen J. Atkinson、Nermina Lamadema、N. Shaun B. Thomas

  DOI：10.1021/acs.jmedchem.5b00545

  日期：2015.9.10

  A novel series of potent chiral inhibitors of histone deacetylase (HDAC) is described that contains an oxazoline capping group and a N-(2-aminophenyl)-benzamide unit. Among several new inhibitors of this type exhibiting Class I selectivity and potent inhibition of HDAC3-NCoR2, in vitro assays for the inhibition of HDAC1, HDAC2, and HDAC3-NCoR2 by N-(2-aminophenyl)-benzamide 15k gave respective IC50 values of 80, 110, and 6 nM. Weak inhibition of all other HDAC isoforms (HDAC4, 5, 6, 7, and 9: IC50 > 100 000 nM; HDAC8: IC50 = 25 000 nM; HDAC10: IC50 > 4000 nM; HDAC11: IC50 > 2000 nM) confirmed the Class I selectivity of 15k 2-Aminoimidazolinyl, 2-thioimidazolinyl, and 2-aminooxazolinyl units were shown to be effective replacements for the pyrimidine ring present in many other 2-(aminophenyl)-benzamides previously reported, but the 2-aminooxazolinyl unit was the most potent in inhibiting HDAC3-NCoR2. Many of the new HDAC inhibitors showed higher solubilities and lower binding to human serum albumin than that of Mocetinostat. Increases in histone H3K9 acetylation in the human cell lines U937 and PC-3 was observed for all three oxazolinyl inhibitors evaluated; those HDAC inhibitors also lowered cyclin E expression in U937 cells but not in PC-3 cells, indicating underlying differences in the mechanisms of action of the inhibitors on those two cell lines.
• US5212192A
  申请人：——

  公开号：US5212192A

  公开（公告）日：1993-05-18