1-(adamantan-1-yl)-3-(3-chlorophenyl)thiourea | 457093-33-3

• 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-(adamantan-1-yl)-3-(3-chlorophenyl)thiourea
• 英文别名: N-(1-Adamantyl)-N'-(3-chlorophenyl)thiourea；1-(1-adamantyl)-3-(3-chlorophenyl)thiourea
• CAS: 457093-33-3
• 化学式: C₁₇H₂₁ClN₂S
• 分子量: 320.886
• InChiKey: QDWKKMPTZMLZQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 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：

  1-(adamantan-1-yl)-3-(3-chlorophenyl)thiourea 、 对溴溴苄 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 3.0h， 生成 (Z)-3-(adamantan-1-yl)-S-(4-bromobenzyl)-1-(3-chlorophenyl)isothiourea
  参考文献：
  名称：

  (Z)-3-(金刚烷-1-基)-1-(苯基或3-氯苯基)-S-(4-溴苄基)异硫脲的X射线和理论研究：涉及弱非共价相互作用、化疗药物的探索活性和 QM/MM 结合能

  摘要：

  摘要 已经对两种金刚烷-异硫脲杂化衍生物的晶体堆积以及已知的密切相关结构进行了详细探索，以描述卤素取代基的影响以及弱分子间相互作用在其超分子结构中的作用。本研究中使用的金刚烷-异硫脲杂化衍生物是( Z )-3-(Adamantan-1-yl) -S- (4-溴苄基)-1-苯基异硫脲( 1 )、C 24 H 27 BrN 2 S和( Z )-3-(金刚烷-1-基) -S- (4-溴苄基)-1-(3-氯苯基)异硫脲( 2 )，C 24 H 26 BrClN 2S，以 X 射线晶体学为特征。X射线结构表明1和2的分子构象不同，并通过分子内C-H···N相互作用稳定。此外，在2中形成了一个短的分子内 H···H 接触。Hirshfeld 表面分析用于描述不同分子间相互作用的性质及其对晶体堆积的贡献。分子二聚体强度的定量分析存在于1和2中已使用 PIXEL 方法执行。静电势图清楚地揭示了 Br 和 Cl

  DOI：

  10.1080/07391102.2020.1840443
• 作为产物：
  描述：

  金刚烷胺 、 3-氯异硫氰酸苯酯 以 乙醇 为溶剂， 生成 1-(adamantan-1-yl)-3-(3-chlorophenyl)thiourea
  参考文献：
  名称：

  (Z)-3-(金刚烷-1-基)-1-(苯基或3-氯苯基)-S-(4-溴苄基)异硫脲的X射线和理论研究：涉及弱非共价相互作用、化疗药物的探索活性和 QM/MM 结合能

  摘要：

  摘要 已经对两种金刚烷-异硫脲杂化衍生物的晶体堆积以及已知的密切相关结构进行了详细探索，以描述卤素取代基的影响以及弱分子间相互作用在其超分子结构中的作用。本研究中使用的金刚烷-异硫脲杂化衍生物是( Z )-3-(Adamantan-1-yl) -S- (4-溴苄基)-1-苯基异硫脲( 1 )、C 24 H 27 BrN 2 S和( Z )-3-(金刚烷-1-基) -S- (4-溴苄基)-1-(3-氯苯基)异硫脲( 2 )，C 24 H 26 BrClN 2S，以 X 射线晶体学为特征。X射线结构表明1和2的分子构象不同，并通过分子内C-H···N相互作用稳定。此外，在2中形成了一个短的分子内 H···H 接触。Hirshfeld 表面分析用于描述不同分子间相互作用的性质及其对晶体堆积的贡献。分子二聚体强度的定量分析存在于1和2中已使用 PIXEL 方法执行。静电势图清楚地揭示了 Br 和 Cl

  DOI：

  10.1080/07391102.2020.1840443

文献信息

• Ultrasonic-assisted synthesis of amantadine derivatives-in vitro urease and α-glucosidase inhibitory activities, mechanistic, and computational studies
  作者：Mohsin Raza、Hina Siddiqui、Majid Khan、Saeed Ullah、Fazila Rizvi、Raheel Ahmad、Ioannis P Gerothanassis、Atia-tul Wahab、M. Iqbal Choudhary

  DOI：10.1016/j.molstruc.2022.133544

  日期：2022.10

  compounds at the active site of the enzymes. The two most active adamantane analogs against urease are those with m- and o-fluoro substitution due to specific interactions with CME592, HOH1918 and GLN635 (3.04, 2.74, and 3.21 Å). Ortho analogs interact with GLN635 (3.04, 3.10 Å). The two analogs having diflouro and tri flouro methyl group, showed a slight lower activity as compared to the first two compounds

  据报道，超声合成26种金刚烷胺衍生物 ( 3-28 )，包括 7 种新化合物，与文献数据相比，合成时间显着缩短，产率百分比提高。这里首次报道了对所有金刚烷胺衍生物的脲酶和α-葡萄糖苷酶抑制活性的评估。与标准药物乙酰氧肟酸（IC 50  = 20.3 ± 0.4 µM） 相比，三种化合物被发现是有效的脲酶抑制剂（IC 50  = 9.32 ± 1.01 µM，至 IC 50 = 11.32 ± 1.05 µM）。与标准药物阿卡波 糖（IC50  = 875.75 ± 2.08 µM）。进行动力学研究以研究α-葡萄糖苷酶的竞争性和非竞争性抑制以及脲酶的混合型抑制。检查所有化合物以及母体药物对人成纤维细胞 (BJ) 细胞系的细胞毒性。四种化合物被发现是有毒的，而其余的是无毒的。 此外，进行了计算机研究以预测化合物在酶活性位点的结合相互作用。由于与 CME592、HOH1918 和 GLN635 的特定相互作用（3
• Compounds for modulating integrin CD11B/CD18
  申请人：The General Hospital Corporation

  公开号：US10408820B2

  公开（公告）日：2019-09-10

  The application describes an assay for the identification of small molecule modulators of integrin CD11b/CD18 and small molecules capable of modulating activity of this receptor. Such compounds may be used in certain embodiments for treating a disease or condition selected from inflammation, immune-related disorders, cancer, ischemia-reperfusion injury, stroke, neointimal thickening associated with vascular injury, bullous pemphigoid, neonatal obstructive nephropathy, and cardiovascular disease, or in other embodiments for the treatment of a disease or condition selected from immune deficiency, acquired immune deficiency syndrome (AIDS), myeloperoxidase deficiency, Wiskott-Aldrich syndrome, chronic granulomatous disease, hyper-IgM syndromes, leukocyte adhesion deficiency, Chediak-Higashi syndrome, and severe combined immunodeficiency.

  该申请描述了一种用于鉴定整合素 CD11b/CD18 小分子调节剂和能够调节该受体活性的小分子的检测方法。在某些实施方案中，此类化合物可用于治疗选自炎症、免疫相关疾病、癌症、缺血再灌注损伤、中风、与血管损伤相关的新内膜增厚、牛皮癣、新生儿阻塞性肾病和心血管疾病的疾病或病症、或在其他实施方案中，用于治疗选自免疫缺陷、获得性免疫缺陷综合征（艾滋病）、髓过氧化物酶缺乏、Wiskott-Aldrich 综合征、慢性肉芽肿病、高 IgM 综合征、白细胞粘附缺陷、Chediak-Higashi 综合征和严重联合免疫缺陷的疾病或病症。
• Compounds for modulating integrin CD11b/CD18
  申请人：Gupta Vineet

  公开号：US20100056503A1

  公开（公告）日：2010-03-04

  The application describes an assay for the identification of small molecule modulators of integrin CD11b/CD18 and small molecules capable of modulating activity of this receptor. Such compounds may be used in certain embodiments for treating a disease or condition selected from inflammation, immune-related disorders, cancer, ischemia-reperfusion injury, stroke, neointimal thickening associated with vascular injury, bullous pemphigoid, neonatal obstructive nephropathy, and cardiovascular disease, or in other embodiments for the treatment of a disease or condition selected from immune deficiency, acquired immune deficiency syndrome (AIDS), myeloperoxidase deficiency, Wiskott-Aldrich syndrome, chronic granulomatous disease, hyper-IgM syndromes, leukocyte adhesion deficiency, Chediak-Higashi syndrome, and severe combined immunodeficiency.
• COMPOUNDS FOR MODULATING INTEGRIN CDIIb/CDI8
  申请人：Gupta Vineet

  公开号：US20130045967A1

  公开（公告）日：2013-02-21

  The application describes an assay for the identification of small molecule modulators of integrin CD11b/CD18 and small molecules capable of modulating activity of this receptor. Such compounds may be used in certain embodiments for treating a disease or condition selected from inflammation, immune-related disorders, cancer, ischemia-reperfusion injury, stroke, neointimal thickening associated with vascular injury, bullous pemphigoid, neonatal obstructive nephropathy, and cardiovascular disease, or in other embodiments for the treatment of a disease or condition selected from immune deficiency, acquired immune deficiency syndrome (AIDS), myeloperoxidase deficiency, Wiskott-Aldrich syndrome, chronic granulomatous disease, hyper-IgM syndromes, leukocyte adhesion deficiency, Chediak-Higashi syndrome, and severe combined immunodeficiency.
• Compounds for Modulating Integrin CD11B/CD18
  申请人：The General Hospital Corporation

  公开号：US20140303026A1

  公开（公告）日：2014-10-09

  The application describes an assay for the identification of small molecule modulators of integrin CD11b/CD18 and small molecules capable of modulating activity of this receptor. Such compounds may be used in certain embodiments for treating a disease or condition selected from inflammation, immune-related disorders, cancer, ischemia-reperfusion injury, stroke, neointimal thickening associated with vascular injury, bullous pemphigoid, neonatal obstructive nephropathy, and cardiovascular disease, or in other embodiments for the treatment of a disease or condition selected from immune deficiency, acquired immune deficiency syndrome (AIDS), myeloperoxidase deficiency, Wiskott-Aldrich syndrome, chronic granulomatous disease, hyper-IgM syndromes, leukocyte adhesion deficiency, Chediak-Higashi syndrome, and severe combined immunodeficiency.