2-Methoxy-10-chloracetyl-phenthiazin | 3534-18-7

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2-Methoxy-10-chloracetyl-phenthiazin
• 英文别名: 10-chloroacetyl-2-methoxy-10H-phenothiazine；2-Chloro-1-(2-methoxyphenothiazin-10-yl)ethanone
• CAS: 3534-18-7
• 化学式: C₁₅H₁₂ClNO₂S
• 分子量: 305.785
• InChiKey: WLYBVXQXBUACDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.06
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-Methoxy-10-chloracetyl-phenthiazin 以69%的产率得到
  参考文献：
  名称：

  SHRIVASTAVA N. M.; SHARMA V. N.; GARG S. P., J. INDIAN CHEM. SOC. , 1975, 52, NO 8, 743-745

  摘要：

  DOI：
• 作为产物：
  描述：

  2-甲氧基酚噻嗪 、 氯乙酰氯 以 甲苯 为溶剂， 以49 %的产率得到2-Methoxy-10-chloracetyl-phenthiazin
  参考文献：
  名称：

  具有新反应基团的 SARS-CoV-2 3C 样蛋白酶抑制剂的发现及机制研究

  摘要：

  3CL pro是治疗 COVID-19 的一个有吸引力的靶点。使用支架跳跃策略，我们鉴定了 3CL pro ( 3a )的有效抑制剂，其含有硫氰酸盐部分作为新型弹头，可以与蛋白质的 Cys145 形成共价键。串联质谱 (MS/MS) 和 X 射线晶体学证实了3a与其催化口袋中的蛋白质之间形成共价键的机制。此外，还设计并合成了化合物3a的几种类似物。其中，化合物3h对3CL pro的抑制效果最好，IC 50为0.322 μM，k inact / K i值为1669.34 M –1 s –1，并且对3CL pro对宿主蛋白酶表现出良好的靶点选择性。化合物3c可抑制 Vero E6 细胞中的 SARS-CoV-2 (EC 50 = 2.499 μM)，且细胞毒性较低 (CC 50 > 200 μM)。这些研究为未来探索和开发新的 3CL前体抑制剂提供了思路和见解。

  DOI：

  10.1021/acs.jmedchem.3c00818

文献信息

• N-Homolupinanoyl and N-(ω-lupinylthio)alkanoyl derivatives of some tricyclic systems as ligands for muscarinic M1 and M2 receptor subtypes
  作者：Bruno Tasso、Anna Sparatore、Fabio Sparatore

  DOI：10.1016/s0014-827x(03)00104-6

  日期：2003.9

  A set of N-homolupinanoyl- and N-(omega-lupinylthio)alkanoyl derivatives of tricyclic systems (as phenothiazine, iminodibenzyl and dihydropyridobenzodiazepinone) has been prepared and tested for affinity for rat muscarinic M(1) and M(2) receptor subtypes labeled with [3H]pirenzepine and [3H]AF-DX 384. Good affinity for both M(1) and M(2) subtypes was displayed by most compounds, often with nanomolar K(i) values, which for lupinylthiopropionyl- and lupinylthiobutyryl-phenothiazines (13-16) were comparable to those of pirenzepine and methoctramine, respectively. However, only moderate selectivity for one or the other subtype was seen.
• [EN] PHENOTHIAZINE ANTIPSYCHOTICS FOR USE IN THE TREATMENT OF GLIOBLASTOMA<br/>[FR] ANTIPSYCHOTIQUES À BASE DE PHÉNOTHIAZINE POUR UTILISATION DANS LE TRAITEMENT DU GLIOBLASTOME
  申请人：[en]VESTLANDETS INNOVASJONSSELSKAP AS

  公开号：WO2023007181A1

  公开（公告）日：2023-02-02

  The invention provides compounds of formula (I), stereoisomers, and pharmaceutically acceptable salts thereof for use in the treatment of cancer: Formula (I) wherein: X is CH, S, N or NH; Z is C or N; A is an optionally substituted amine or an optionally substituted carbocyclic or heterocyclic ring system; L is a linking group which is an optionally substituted C1-6alkylene group in which one or more -CH2-groups of the alkylene chain may be replaced by a group independently selected from -O-, -S- and -NR'- (where R' is H or C1-3alkyl); each R1is independently selected from: C1-6alkyl, C2-6alkenyl, C2-6alkynyl, C1-6haloalkyl, -O-C1-6alkyl, -S-C1-6alkyl, -OH, -SH, halogen, and an optionally substituted aryl group; n is an integer from 0 to 4; R3and R4are each independently selected from: hydrogen, C2-6alkenyl, and C2-6alkynyl, or R3and R4, together with the intervening ring carbon atoms, form an optionally substituted aryl ring; and represents an optional bond between two adjacent carbon atoms in the ring. The compounds of formula (I), their stereoisomers and pharmaceutically acceptable salts find particular use in the treatment of glioblastoma.