2-cyano-N-(5-methyl-1,3,4-thiadiazol-2-yl)acetamide | 90158-74-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-cyano-N-(5-methyl-1,3,4-thiadiazol-2-yl)acetamide
• CAS: 90158-74-0
• 化学式: C₆H₆N₄OS
• mdl: MFCD01350985
• 分子量: 182.206
• InChiKey: QGRUGDKIOYQZQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-cyano-N-(5-methyl-1,3,4-thiadiazol-2-yl)acetamide 在 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 4-methyl-5-methylene-1-(5-methyl[1,3,4]thiadiazol-2-yl)-2-oxo-2,5-dihydro-1H-pyrrole-3-carbonitrile
  参考文献：
  名称：

  Synthesis of N-Substituted γ-Methylene γ-Lactams

  摘要：

  在碱催化下，N-取代氰基乙酰胺 1 与 1,2-二酮 2 缩合生成γ-羟基γ-内酰胺 3。用酸处理 3 可以得到新型杀菌的γ-亚甲基γ-内酰胺 4。4b 的外环双键与 4-甲苯亚磺酸盐发生了可逆反应。

  DOI：

  10.1071/ch05286
• 作为产物：
  描述：

  2-氨基-5-甲基-1,3,4-噻二唑 、 氰乙酸 在 N,N'-二异丙基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以78%的产率得到2-cyano-N-(5-methyl-1,3,4-thiadiazol-2-yl)acetamide
  参考文献：
  名称：

  Synthesis of N-Substituted γ-Methylene γ-Lactams

  摘要：

  在碱催化下，N-取代氰基乙酰胺 1 与 1,2-二酮 2 缩合生成γ-羟基γ-内酰胺 3。用酸处理 3 可以得到新型杀菌的γ-亚甲基γ-内酰胺 4。4b 的外环双键与 4-甲苯亚磺酸盐发生了可逆反应。

  DOI：

  10.1071/ch05286

文献信息

• [EN] 3-PHENYL-N- ((1, 3, 4) THIADIAZOL-2-YL) -ACRYLAMIDE DERIVATIVES AND RELATED COMPOUNDS AS MODULATORS OF ESTROGEN-RELATED RECEPTORS FOR THE TREATMENT OF E.G. CANCER, RHEUMATOID ARTHRITIS OR NEUROLOGICAL DISORDERS<br/>[FR] DERIVES DE 3-PHENYL-N- ((1, 3, 4) THIADIAZOL-2-YL) -ACRYLAMIDE ET COMPOSES APPARENTES UTILES COMME MODULATEURS DES RECEPTEURS LIES A L'OESTROGENE DANS LE TRAITEMENT DU CANCER, DE L'ARTHRITE RHUMATOIDE OU DE TROUBLES NEUROLOGIQUES
  申请人：X CEPTOR THERAPEUTICS INC

  公开号：WO2005072731A1

  公开（公告）日：2005-08-11

  Compounds of formula (I) are provided as well as compositions and methods of using compounds of formula (I) for modulating the activity of the estrogen-related receptors and for the treatment, prevention, or amelioration of one or more symptoms of disease or disorder related to the activity of the estrogen-related receptor. Considering the wide range of activity of the nuclear hormone receptor ERRα, the compounds described herein which are capable of modulating ERRα activity, are useful for treating a range of disease states including cancer, diabetes, obesity, hyperlipidermia, arthritis, atherosclerosis, osteoporosis, anxiety, depression, Parkinson’s disease and Alzheimer’s disease. Formula (I). The substituents are defined in the claims.

  提供了化学式（I）的化合物，以及使用化学式（I）的化合物调节雌激素相关受体活性的组合物和方法，用于治疗、预防或改善与雌激素相关受体活性有关的一种或多种疾病或紊乱的症状。考虑到核激素受体ERRα的广泛活性范围，本文描述的能够调节ERRα活性的化合物，可用于治疗包括癌症、糖尿病、肥胖、高脂血症、关节炎、动脉粥样硬化、骨质疏松症、焦虑、抑郁症、帕金森病和阿尔茨海默病在内的一系列疾病状态。化学式（I）。取代基在权利要求中有定义。
• A novel class of selective CK2 inhibitors targeting its open hinge conformation
  作者：Andrea Dalle Vedove、Francesca Zonta、Enrico Zanforlin、Nicola Demitri、Giovanni Ribaudo、Giulia Cazzanelli、Alberto Ongaro、Stefania Sarno、Giuseppe Zagotto、Roberto Battistutta、Maria Ruzzene、Graziano Lolli

  DOI：10.1016/j.ejmech.2020.112267

  日期：2020.6

  Its inhibitor SRPIN803, based on a 6-methylene-5-imino-1,3,4-thiadiazolopyrimidin-7-one scaffold, showed notable specificity. Our synthesis of the initially proposed SRPIN803 resulted in its constitutional isomer SRPIN803-revised, where the 2-cyano-2-propenamide group does not cyclise and fuse to the thiadiazole ring. Its crystallographic structure in complex with CK2α identifies the structural determinants

  蛋白激酶CK2维持癌症的生长，特别是在血液系统恶性肿瘤中。其抑制剂SRPIN803基于6-亚甲基-5-亚氨基-1,3,4-噻二唑并吡啶亚胺-7-7骨架，表现出显着的特异性。我们最初提出的SRPIN803的合成导致其结构异构体SRPIN803进行了修订，其中2-氰基-2-丙烯酰胺基团不环化并与噻二唑环融合。与CK2α配合​​形成的晶体结构确定了报道的特异性的结构决定因素。SRPIN803修订版探讨了CK2开放铰链构象，这种结构在激酶中极为罕见，并且也与该区域的侧链相互作用。它的优化产生了更有效的化合物4，该化合物抑制细胞内CK2，显着影响肿瘤细胞的活力，并在一组320种激酶上显示出显着的选择性。
• 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.
• WALKER, G. N.
  作者：WALKER, G. N.

  DOI：——

  日期：——