1-benzylimidazolidine-2-thione | 123566-44-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-benzylimidazolidine-2-thione
• CAS: 123566-44-9
• 化学式: C₁₀H₁₂N₂S
• 分子量: 192.285
• InChiKey: XNPVCJCUZCIAIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  47.4
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-benzylimidazolidine-2-thione 、 7-chloro-3-(chloromethyl)-5H-thiazolo[2,3-b]quinazoline hydrochloride 在 盐酸 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 168.0h， 以12%的产率得到3-(((1-benzyl-4,5-dihydro-1H-imidazol-2-yl)thio)methyl)-7-chloro-5H-thiazolo[2,3-b]quinazoline dihydrochloride
  参考文献：
  名称：

  [EN] CYCLIC ISOTHIOUREA DERIVATIVES AS CXCR4 MODULATORS
  [FR] DÉRIVÉS D'ISOTHIO-URÉE CYCLIQUES UTILISÉS COMME MODULATEURS DU CXCR4

  摘要：

  本发明提供了式（I）的新化合物和含有这些化合物的药物组合物。式（I）的化合物可以作为CXCR4调节剂，特异性靶向CXCR4小口袋，并且已经发现它们抑制免疫细胞中炎性细胞因子的产生，这使得这些化合物在治疗中具有极大的优势，特别是在治疗或预防炎症性疾病、自身免疫性疾病、自身炎症性疾病或干扰素病中，例如系统性红斑狼疮、皮肌炎或类风湿性关节炎。

  公开号：

  WO2022064075A1
• 作为产物：
  描述：

  N-苄基乙二胺 在 N-甲基吡咯烷酮 作用下， 以 乙酸乙酯 为溶剂， 反应 0.25h， 生成 1-benzylimidazolidine-2-thione
  参考文献：
  名称：

  Some benzyl-substituted imidazoles, triazoles, tetrazoles, pyridinethiones, and structural relatives as multisubstrate inhibitors of dopamine .beta.-hydroxylase. 4. Structure-activity relationships at the copper binding site

  摘要：

  Structure-activity relationships (SAR) were determined for novel multisubstrate inhibitors of dopamine beta-hydroxylase (DBH; EC 1.14.17.1) by examining the effects upon in vitro inhibitory potencies resulting from structural changes at the copper-binding region of inhibitor. Attempts were made to determine replacement groups for the thione sulfur atom of the prototypical inhibitor 1-(4-hydroxybenzyl)imidazole-2-thione described previously. The synthesis and evaluation of oxygen and nitrogen analogues of the soft thione group demonstrated the sulfur atom to be necessary for optimal activity. An additional series of imidazole-2-thione relatives was prepared in an effort to probe the relationship between the pKa of the ligand group and inhibitory potency. In vitro inhibitory potency was shown not to correlate with ligand pKa over a range of approximately 10 pKa units, and a rationale for this is advanced. Additional ligand modifications were prepared in order to explore bulk tolerance at the enzyme oxygen binding site and to determine the effects of substituting a six-membered ligand group for the five-membered imidazole-2-thione ligand.

  DOI：

  10.1021/jm00164a051

文献信息

• [EN] POLYCYCLIC COMPOUNDS, TERMED CALIXURENES, AND USES THEREOF<br/>[FR] COMPOSÉS POLYCYCLIQUES APPELÉS CALIXURÈNES ET LEURS UTILISATIONS
  申请人：TECHNION RES & DEV FOUNDATION

  公开号：WO2011018790A1

  公开（公告）日：2011-02-17

  Disclosed is a novel family of macrocyclic compounds, coined calixurenes, which comprises linear and cyclic oligomers composed of alternating moieties of an aromatic unit and a ureatic unit, linked to one another via a bridging moiety. The disclosed calixurenes feature multiple heteroatom-containing groups, and can be designed so as to feature other functionalities, and can thus be used in a variety of applications. Further disclosed are processes of preparing the calixurenes, articles containing same and uses thereof.

  披露了一类新颖的大环化合物家族，被称为卡利克烷（calixurenes），包括由芳香基团和脲基团交替组成的线性和环状寡聚物，通过桥接基团相互连接。披露的卡利克烷具有多个含杂原子的基团，并可设计为具有其他功能，因此可用于各种应用。进一步披露了制备卡利克烷的方法、含有卡利克烷的物品以及其用途。
• 1-aralkyl-2-mercaptoimidazolines as DBH inhibitors
  申请人：SmithKline Beckman Corporation

  公开号：US04876266A1

  公开（公告）日：1989-10-24

  Disclosed are novel substituted 3-aralkylimidazolines of the structure. ##STR1## processes for their preparation, intermediates useful in their preparation, pharmaceutical compositions containing them and their use in therapy in particular as dopamine-.beta.-hydroxylase inhibitors.

  本发明涉及一种新的取代3-芳基咪唑啉结构，其制备方法，制备中有用的中间体，含有它们的制药组合物以及它们在治疗中的应用，特别是作为多巴胺-β-羟化酶抑制剂。
• Thiocarbonyl fluoride generated in situ from difluorocarbene for cyclization of vicinal X-H substituted amines (X = N, O or S)
  作者：Jia-Lu Hu、Mu-Xian Fu、Ji-Chang Xiao、Jin-Hong Lin

  DOI：10.1016/j.jfluchem.2023.110212

  日期：2023.11

  for the cyclization of vicinal X-H substituted amines to provide various five-membered heterocycles. However, aryl amines are required to be used and difluoromethylation of the NH bond or a newly generated S-H bond cannot be suppressed. Herein we describe the use of thiocarbonyl fluoride generated in situ as a thiocarbonyl source for the cyclization of vicinal X-H substituted alkyl amines (X = N, O

  二氟碳烯已成为有机合成中的通用中间体。我们之前发现的二氟卡宾转化为硫代碳酰氟的方法可以开发为邻位XH取代胺环化的合成工具，以提供各种五元杂环。然而，需要使用芳基胺并且不能抑制NH键或新生成的SH键的二氟甲基化。在此，我们描述了使用原位生成的硫代羰基氟作为硫代羰基源，用于环化邻位XH取代的烷基胺（X  =N 、 O、S）以提供咪唑烷-2-硫酮、恶唑烷-2-硫酮和噻唑烷-2 -硫酮。使用烷基胺构建与由芳基胺获得的杂环不同的杂环。游离的NH键保持完整，没有被二氟甲基化。
• Substituted 1-aralkyl imidazoline-2-thiols
  申请人：SMITHKLINE BECKMAN CORPORATION

  公开号：EP0329900A1

  公开（公告）日：1989-08-30

  Compounds of structure (I) and pharmaceutically acceptable salts thereof are described in which, n is 0 to 5; X¹ to X⁵ are any accessible combination of hydrogen, halogen, C₁₋₆alkyl, C₁₋₄alkoxy, cyano, nitro, SONH₂, SO₂CH₃, SO₂CH₂F, SO₂CHF₂, SO₂CF₃, CF₃, CHO, OH, (CH₂)OH, CO₂H, or CO₂CpH2p+1wherein p is 1 to 4; R is hydrogen, C₁₋₄alkyl or (CH₂)m-CO₂R¹; m is 0 to 5; and R¹ is H or C₁₋₄alkyl. These compounds are dopamine-β-hydroxylase inhibitors. Pharmaceutical compositions are described as are methods of use. Processes for the preparation of these compounds are described.

  结构(I)的化合物 及其药学上可接受的盐类，其中，n 为 0 至 5；X¹ 至 X⁵ 是氢、卤素、C₁₋₆烷基、C₁₋₄烷氧基、氰基、硝基、SONH₂、SO₂CH₃、SO₂CH₂F、SO₂CHF₂、SO₂CF₃、CF₃、CHO、OH、(CH₂)OH、CO₂H 或 CO₂CpH2p+1，其中 p 为 1 至 4；R 是氢、C₁₋₄烷基或 (CH₂)m-CO₂R¹；m 是 0 至 5；R¹ 是 H 或 C₁₋₄ 烷基。 这些化合物是多巴胺-β-羟化酶抑制剂。药剂组合物和使用方法均有描述。还描述了制备这些化合物的工艺。
• Inhibitory effect of novel tetrahydropyrimidine-2(1H)-thiones on melanogenesis
  作者：P. Thanigaimalai、Ki-Cheul Lee、Seong-Cheol Bang、Jee-Hyun Lee、Cheong-Yong Yun、Eunmiri Roh、Bang-Yeon Hwang、Youngsoo Kim、Sang-Hun Jung

  DOI：10.1016/j.bmc.2009.12.044

  日期：2010.2

  The series of imidazoldine-2-thiones 2 and tetrahydropyrimidine-2-thiones 3 were discovered as inhibitor of alpha-MSH-induced melanin production in melanoma B16 cells. The primary bioassay showed that 1-(4-ethylbenzyl)-tetrahydropyrimidine-2(1H)-thione 3e (> 100% inhibition at 10 mu M, IC50 = 1.2 mu M) and 1-(4-tert-butylbenzyl)-tetrahydropyrimidine-2(1H)-thione 3f (> 100% inhibition at 10 mu M, IC50 = 0.76 mu M) exhibited potent inhibitory effect against alpha-MSH-induced melanin production. Compounds 3 inhibit the biosynthesis of tyrosinase without affecting its catalytic activity in melanogenesis. (C) 2010 Elsevier Ltd. All rights reserved.