5-(4-甲基苄基)-1,3,4-噻二唑-2-胺 | 39181-45-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 5-(4-甲基苄基)-1,3,4-噻二唑-2-胺
• 中文别名: [5-(4-甲苄基)-1,3,4-噻二唑-2-基]胺
• 英文名称: 2-amino-5-(4-methylbenzyl)-1,3,4-thiadiazole
• 英文别名: 5-(4-Methylbenzyl)-1,3,4-thiadiazol-2-amine；5-[(4-methylphenyl)methyl]-1,3,4-thiadiazol-2-amine
• CAS: 39181-45-8
• 化学式: C₁₀H₁₁N₃S
• mdl: MFCD02664087
• 分子量: 205.283
• InChiKey: NKGWYLDUGQTJMM-UHFFFAOYSA-N

物化性质

• 熔点：
  208-212 °C(Solv: ethanol (64-17-5))
• 沸点：
  395.6±45.0 °C(Predicted)
• 密度：
  1.256±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  80
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  5-(4-甲基苄基)-1,3,4-噻二唑-2-胺 在 盐酸 、 copper(l) chloride 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 1.0h， 生成 2-chloro-5-(4-methylbenzyl)-1,3,4-thiadiazole
  参考文献：
  名称：

  [EN] 1,3-DISUBSTITUTED HETEROARYL NMDA/NR2B ANTAGONISTS
  [FR] ANTAGONISTES DE NMDA/NR2B À BASE D'HÉTÉROARYLES 1,3-DISUBSTITUÉS

  摘要：

  公开号：

  WO2006017409A3
• 作为产物：
  描述：

  对甲基苯乙酸 、 氨基硫脲 在 硫酸 作用下， 以52%的产率得到5-(4-甲基苄基)-1,3,4-噻二唑-2-胺
  参考文献：
  名称：

  新型2-芳烷基-5-取代-6-（4'-氟苯基）-咪唑并[2,1-b] [1,3,4]噻二唑衍生物的合成及生物学评价

  摘要：

  咪唑并[2,1-b]噻唑衍生物左旋咪唑据报道是潜在的抗肿瘤药。在本研究中，我们合成，表征和评估了其新类似物的化学活性，这些新类似物在芳烷基中和具有相同化学主链但侧链不同的咪唑并噻二唑分子即2-芳烷基-6-（4'-氟苯基）-咪唑上具有取代作用[2,1-b] [1,3,4]噻二唑（SCR1），2-芳烷基-5-溴-6-（4'-氟苯基）-咪唑[2,1-b] [1,3,4 ]-噻二唑（SCR2），2-芳烷基-5-甲酰基-6-（4'-氟苯基）-咪唑[2,1-b] [1,3,4]-噻二唑（SCR3）和2-芳烷基-5 -白血病细胞上的-thiocyanato-6-（4'-氟苯基）-咪唑并[2,1-b] [1,3,4]-噻二唑（SCR4）。细胞毒性研究表明3a，4a和4c表现出很强的细胞毒性，而其他的则具有中等的细胞毒性。在这些我们选择了图4a（IC 50，μM8）为理解它的细胞毒性的机制。FACS分析结合

  DOI：

  10.1016/j.ejmech.2011.02.064

文献信息

• 1,3-Disubstituted Heteroaryl Nmda/Nr2b Antagonists
  申请人：Layton E. Mark

  公开号：US20070293515A1

  公开（公告）日：2007-12-20

  Compounds represented by Formula I: (wherein A, B, D, P, Q, R 1 , R 2 , R 3 , W and Y are described herein) or pharmaceutically acceptable salts thereof, are effective as NMDA/NR2B antagonists useful for treating neurological conditions such as, for example, pain, Parkinson's disease, Alzheimer's disease, epilepsy, depression, anxiety, ischemic brain injury including stroke, and other conditions.

  公式I所代表的化合物（其中A、B、D、P、Q、R1、R2、R3、W和Y的描述如下）或其药学上可接受的盐，可作为有效的NMDA / NR2B拮抗剂，用于治疗神经系统疾病，例如疼痛，帕金森病，阿尔茨海默病，癫痫，抑郁症，焦虑症，缺血性脑损伤包括中风和其他疾病。
• Divergent effects of compounds on the hydrolysis and transpeptidation reactions of γ-glutamyl transpeptidase
  作者：Stephanie Wickham、Nicholas Regan、Matthew B. West、Vidya Prasanna Kumar、Justin Thai、Pui Kai Li、Paul F. Cook、Marie H. Hanigan

  DOI：10.3109/14756366.2011.597748

  日期：2012.8.1

  A novel class of inhibitors of the enzyme gamma-glutamyl transpeptidase (GGT) were evaluated. The analog OU749 was shown previously to be an uncompetitive inhibitor of the GGT transpeptidation reaction. The data in this study show that it is an equally potent uncompetitive inhibitor of the hydrolysis reaction, the primary reaction catalyzed by GGT in vivo. A series of structural analogs of OU749 were evaluated. For many of the analogs, the potency of the inhibition differed between the hydrolysis and transpeptidation reactions, providing insight into the malleability of the active site of the enzyme. Analogs with electron withdrawing groups on the benzosulfonamide ring, accelerated the hydrolysis reaction, but inhibited the transpeptidation reaction by competing with a dipeptide acceptor. Several of the OU749 analogs inhibited the transpeptidation reaction by slow onset kinetics, similar to acivicin. Further development of inhibitors of the GGT hydrolysis reaction is necessary to provide new therapeutic compounds.
• Synthesis of (1,3,4-thiadiazol-2-yl)-acrylamide derivatives as potential antitumor agents against acute leukemia cells
  作者：Qing Li、Ran An、Yaochun Xu、Mi Zhou、Yan Li、Chun Guo、Renxiao Wang

  DOI：10.1016/j.bmcl.2020.127114

  日期：2020.5

  A lead compound with the (1,3,4-thiadiazol-2-yl) acrylamide scaffold was discovered to have significant cytotoxicity on several tumor cell lines in an in-house cell-based screening. A total of 60 derivative compounds were then synthesized and tested in a CCK-8 cell viability assay. Some of them exhibited improved cytotoxic activities. The most potent compounds had IC50, values of 1-5 mu M on two acute leukemia tumor cell lines, i.e. RS4;11 and HL-60. Flow cytometry analysis of several active compounds and detection of caspase activation indicated that they induced caspase-dependent apoptosis. It was also encouraging to observe that these compounds did not have obvious cytotoxicity on normal cells, i.e. IC50 > 50 mu M on HEK-293T cells. Although the molecular targets of this class of compound are yet to be revealed, our current results suggest that this class of compound represents a new possibility for developing drug candidates against acute leukemia.
• Karki, Subhas S.; Rana, Vivek; Sivan, Ramjith U., Acta poloniae pharmaceutica, 2015, vol. 72, # 5, p. 931 - 936
  作者：Karki, Subhas S.、Rana, Vivek、Sivan, Ramjith U.、Kumar, Sujeet、Renuka, Vinayakumar、Ramareddy, Sureshbabu A.、Subbarao, Prasanna G.、Si, Sudam C.

  DOI：——

  日期：——
• Kumar, Sujeet; Metikurki, Basavaraj; Bhadauria, Vivek Singh, Acta poloniae pharmaceutica, 2016, vol. 73, # 4, p. 913 - 929
  作者：Kumar, Sujeet、Metikurki, Basavaraj、Bhadauria, Vivek Singh、De Clercq, Erik、Schols, Dominique、Tokuda, Harukuni、Karki, Subhas S.

  DOI：——

  日期：——