1-(5-amino-2-methyl-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)-ethan-1-one | 72926-06-8

• 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-(5-amino-2-methyl-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)-ethan-1-one
• 英文别名: 3-acetyl-5-amino-2,3-dihydro-2-methyl-2-phenyl-1,3,4-thiadiazole；1-(5-Amino-2-methyl-2-phenyl-[1,3,4]thiadiazol-3-yl)-ethanone；1-(5-amino-2-methyl-2-phenyl-1,3,4-thiadiazol-3-yl)ethanone
• CAS: 72926-06-8
• 化学式: C₁₁H₁₃N₃OS
• 分子量: 235.31
• InChiKey: FRTKRAYLCPSCAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  84
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  1-(5-amino-2-methyl-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)-ethan-1-one 在 sodium hydroxide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 C₂₁H₁₇ClN₄O₂S₂
  参考文献：
  名称：

  Corrigendum to “Design and synthesis of novel thiadiazole-thiazolone hybrids as potential inhibitors of the human mitotic kinesin Eg5 [Bioorg Med Chem Lett 28 (17) (2018) 2930–2938]”

  摘要：

  DOI：

  10.1016/j.bmcl.2018.08.029
• 作为产物：
  描述：

  N-(4-乙酰基-4,5-二氢-5-甲基-5-苯基-1,3,4-噻二唑-2-基)乙酰胺 在 一水合肼 作用下， 反应 3.0h， 以75%的产率得到1-(5-amino-2-methyl-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)-ethan-1-one
  参考文献：
  名称：

  Synthesis of 4-acyl-2-(acylamino)-.DELTA.2-1,3,4-thiadiazolines and 4-acyl-2-amino-.DELTA.2-1,3,4-thiadiazolines by acylation of thiosemicarbazones

  摘要：

  DOI：

  10.1021/jo01296a025

文献信息

• Thiadiazoline derivative
  申请人：Murakata Chikara

  公开号：US20070112044A1

  公开（公告）日：2007-05-17

  An antitumor agent comprising a thiadiazoline derivative represented by the general formula (I), or a pharmacologically acceptable salt thereof as an active ingredient: (wherein Z represents a sulfur atom and the like, R 1 represents substituted or unsubstituted lower alkynyl and the like, R 2 represents a hydrogen atom and the like, R 3 represents substituted or unsubstituted lower alkyl and the like, and R 4 represents substituted or unsubstituted aryl and the like), and the like are provided.

  一种抗肿瘤剂，包括由通式（I）表示的噻二唑衍生物或其药学上可接受的盐作为活性成分：（其中Z代表硫原子等，R1代表取代或未取代的较低炔基等，R2代表氢原子等，R3代表取代或未取代的较低烷基等，R4代表取代或未取代的芳基等）等。
• THIADIAZOLINE DERIVATIVES
  申请人：KYOWA HAKKO KOGYO CO., LTD.

  公开号：EP1671957A1

  公开（公告）日：2006-06-21

  An antitumor agent comprising a thiadiazoline derivative represented by the general formula (I), or a pharmacologically acceptable salt thereof as an active ingredient: (wherein Z represents a sulfur atom and the like, R1 represents substituted or unsubstituted lower alkynyl and the like, R2 represents a hydrogen atom and the like, R3 represents substituted or unsubstituted lower alkyl and the like, and R4 represents substituted or unsubstituted aryl and the like), and the like are provided.

  一种抗肿瘤制剂，其活性成分包括通式 (I) 所代表的噻二唑啉衍生物或其药理上可接受的盐： (其中 Z 代表硫原子等，R1 代表取代或未取代的低级炔基等，R2 代表氢原子等，R3 代表取代或未取代的低级烷基等，R4 代表取代或未取代的芳基等）等。
• Synthesis of 4-acyl-2-(acylamino)-.DELTA.2-1,3,4-thiadiazolines and 4-acyl-2-amino-.DELTA.2-1,3,4-thiadiazolines by acylation of thiosemicarbazones
  作者：Seiju Kubota、Yasufumi Ueda、Kazuichi Fujikane、Kouhei Toyooka、Masayuki Shibuya

  DOI：10.1021/jo01296a025

  日期：1980.4
• Design and synthesis of novel thiadiazole-thiazolone hybrids as potential inhibitors of the human mitotic kinesin Eg5
  作者：Samukelisiwe Pretty Khathi、Balakumar Chandrasekaran、Sivanandhan Karunanidhi、Chuin Lean Tham、Frank Kozielski、Nisar Sayyad、Rajshekhar Karpoormath

  DOI：10.1016/j.bmcl.2018.07.007

  日期：2018.9

  A novel series of 1,3,4-thiadiazole-thiazolone hybrids 5a-v were designed, synthesized, characterized, and evaluated against the basal and the microtubule (MT)-stimulated ATPase activity of Eg5. From the evaluated derivatives, 5h displayed the highest inhibition with an IC50 value of 13.2 mu M against the MT-stimulated Eg5 ATPase activity. Similarly, compounds 5f and 5i also presented encouraging inhibition with IC50 of 17.2 mu M and 20.2 mu M, respectively. A brief structure-activity relationship (SAR) analysis indicated that 2-chloro and 4-nitro substituents on the phenyl ring of the thiazolone motif contributed significantly to enzyme inhibition. An in silico molecular docking study using the crystal structure of Eg5 further supported the SAR and reasoned the importance of crucial molecular protein-ligand interactions in influencing the inhibition of the ATPase activity of Eg5. The magnitude of the electron-withdrawing functionalities over the hybrids and the critical molecular interactions contributed towards higher in vitro potency of the compounds. The drug-like properties of the synthesized compounds 5a-v were also calculated based on the Lipinski's rule of five and in silico computation of key pharmacokinetic parameters (ADME). Thus, the present work unveils these hybrid molecules as novel Eg5 inhibitors with promising drug-like properties for future development.
• M-STAGE KINESIN INHIBITOR
  申请人：Kyowa Hakko Kirin Co., Ltd.

  公开号：EP1616866B1

  公开（公告）日：2011-12-14