1,3-Dimethyl-4-phenylimidazolin-2-thion | 25433-16-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,3-Dimethyl-4-phenylimidazolin-2-thion
• 英文别名: 1.3-Dimethyl-4(5)-phenyl-imidazolin-2(3)-thion；1.3-Dimethyl-4-phenyl-2-thioxo-Δ(4)-imidazolin；1,3-dimethyl-4-phenyl-1,3-dihydro-imidazole-2-thione；1,3-Dimethyl-4-phenyl-4-imidazoline-2-thione；1,3-dimethyl-4-phenylimidazole-2-thione
• CAS: 25433-16-3
• 化学式: C₁₁H₁₂N₂S
• 分子量: 204.296
• InChiKey: PFZYPHBIKQHBFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  38.6
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  对甲苯磺酸甲酯 、 1,3-Dimethyl-4-phenylimidazolin-2-thion 以 丙酮 为溶剂， 生成
  参考文献：
  名称：

  Specific Molecular Orbital Contributions to Nucleophilicity. The Thiocarbonyl Group as Priviledged Monitor to Pinpoint Active and Less Active Molecular Orbitals in Reactions with Methylating Agents

  摘要：

  The rate constants for 41 compounds bearing a C=S function reacting with MeX (X = I, Tos) span 7 orders of magnitude. The PES spectra of these compounds display two very low energy peaks, which stand clearly apart from the other peaks. These two peaks correspond to the pi orbitals of the C-S group; one is its CS pi bonding orbital oriented out of the molecular plane (pi(CS)) and the other its p-type in-plane lone pair orbital (pi(S)). For some of the compounds, the HOMO is the pi(CS) orbital and for others the HOMO is the ns lone pair orbital. The best correlation (R = 0.96) between rate constants h and PES data is obtained when In(k) is plotted against the inverse of PES energy of the pi(S) lone pair orbital. Whether this lone pair orbital is the HOMO or the next lower HOMO has no importance. A modest correlation (R = 0.78) is obtained when In(k) is plotted against the inverse of PES energy of the pi(CS) bonding orbital, An attempt to correlate the calculated energy of the third highest occupied orbital (from AM1 calculations) with In(h) provides a complete scattering of data (R < 0.1), but the calculated energy of the second lone pair orbital sigma(S) (approximate to 90 kcal mol-l deeper than the HOMO) correlates reasonably with In(h) (R = 0.88). The energies of the S 2s and 2p core orbitals (calculated for 13 cyclic compounds with the HF/3-21G technique to be 4000 to 5500 kcal mol(-1) deeper than HOMO) correlate with In(k) (R = 0.86) as well as does that of the second lone pair orbital os. These results are the first where both frontier orbitals and core orbitals display correlation with overall reactivity. They are discussed in terms of direct (perturbational) versus indirect (nonperturbational) concepts.

  DOI：

  10.1021/jo00113a010

文献信息

• Methods and compositions for the treatment of autoimmune and inflammatory diseases associated with toll-like receptors
  申请人：The Interthyr Corporation

  公开号：EP2399578A1

  公开（公告）日：2011-12-28

  The present invention relates to the treatment of autoimmune and/or inflammatory diseases associated with over-expression of Toll-like receptor 3 (TLR3) as well as Toll-like receptor 4 (TLR4) and/or TLR3/TLR4 signaling in nonimmune cells, monocytes, macrophages, and/or dendritic cells in association with related pathologies. This invention also relates to the use of phenylmethimazoles, methimazole derivatives, and tautomeric cyclic thiones for the treatment of autoimmune and inflammatory diseases associated with Toll-like receptor 3 (TLR3) as well as Toll-like receptor 4 (TLR4) and/or TLR3/TLR4 signaling in nonimmune cells, monocytes, macrophages, and/or dendritic cells in association with related pathologies. This invention also relates to treating a subject having a disease or condition associated with abnormal Toll-like receptor 3 as well as Toll-like receptor 4 and/or TLR3/TLR4 signaling in nonimmune cells, monocytes, macrophages, and/or dendritic cells in association with related pathologies. The present invention also relates to the treatment of autoimmune-inflammatory pathologies and chemokine and cytokine-mediated diseases associated with TLR overexpression and signaling. This invention also relates to pharmaceutical formulations capable of inhibiting the IRF-3/Type 1 IFN/STAT/ISRE/IRF-1 pathway associated with the Toll-like receptor overexpression or signaling.

  本发明涉及治疗与非免疫细胞、单核细胞、巨噬细胞和/或树突状细胞中Toll样受体3（TLR3）以及Toll样受体4（TLR4）和/或TLR3/TLR4信号过度表达有关的自身免疫性和/或炎症性疾病，以及相关病理。本发明还涉及苯基甲巯咪唑、甲巯咪唑衍生物和同分异构环硫代甲烷用于治疗与非免疫细胞、单核细胞、巨噬细胞和/或树突状细胞中的Toll样受体3（TLR3）以及Toll样受体4（TLR4）和/或TLR3/TLR4信号转导相关的自身免疫性和炎症性疾病。本发明还涉及治疗与非免疫细胞、单核细胞、巨噬细胞和/或树突状细胞中 Toll 样受体 3 以及 Toll 样受体 4 和/或 TLR3/TLR4 信号异常有关的疾病或病症。本发明还涉及治疗与 TLR 过度表达和信号转导相关的自身免疫炎症性病症以及趋化因子和细胞因子介导的疾病。本发明还涉及能够抑制与 Toll 样受体过度表达或信号转导相关的 IRF-3/1型 IFN/STAT/ISRE/IRF-1 通路的药物制剂。
• Immune activation by double-stranded polynucleotides
  申请人：Kohn D. Leonard

  公开号：US20050036993A1

  公开（公告）日：2005-02-17

  Double-stranded polynucleotide activates the expression of immune recognition molecules. The polynucleotide can have a minimal length and activates the expression of molecules not encoded by a nucleotide sequence that is not necessarily related to the polynucleotide. The present invention provides for a simple and specific system to activate expression of Class I and/or Class II molecules of the major histocompatibility complex (MHC), and allows regulation of expression of MHC molecules on the cell-surface of antigen presenting cells and other immune cells. Also provided are systems for the screening, identification, and isolation of compounds that increase or decrease this activation.

  双链多核苷酸可激活免疫识别分子的表达。多核苷酸可以具有最小长度，并能激活与多核苷酸不一定相关的核苷酸序列未编码的分子的表达。本发明提供了一种激活主要组织相容性复合体（MHC）I 类和/或 II 类分子表达的简单而特异的系统，可以调节抗原呈递细胞和其他免疫细胞细胞表面 MHC 分子的表达。此外，还提供了用于筛选、鉴定和分离增加或减少这种激活的化合物的系统。
• EP1030909A4
  申请人：——

  公开号：EP1030909A4

  公开（公告）日：2005-11-16
• IMMUNE ACTIVATION BY DOUBLE-STRANDED POLYNUCLEOTIDES
  申请人：KOHN, Leonard D.

  公开号：EP1030909A1

  公开（公告）日：2000-08-30
• METHIMAZOLE DERIVATIVES AND TAUTOMERIC CYCLIC THIONES TO TREAT AUTOIMMUNE DISEASES
  申请人：Sentron Medical, Inc.

  公开号：EP1112072A2

  公开（公告）日：2001-07-04