1-(5-chloro-1,3-benzothiazol-2-yl)piperazine | 232262-76-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1-(5-chloro-1,3-benzothiazol-2-yl)piperazine
• 英文别名: 5-chloro-2-piperazin-1-yl-benzothiazole；5-chloro-2-piperazin-1-yl-1,3-benzothiazole
• CAS: 232262-76-9
• 化学式: C₁₁H₁₂ClN₃S
• 分子量: 253.755
• InChiKey: GRPAYAOSHWYGDG-UHFFFAOYSA-N

物化性质

• 熔点：
  128-132 °C
• 沸点：
  402.1±55.0 °C(Predicted)
• 密度：
  1.360±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  56.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(5-chloro-1,3-benzothiazol-2-yl)piperazine 在 氢气 、 镍 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  Structure Modifications of 6-Aminoquinolones with Potent Anti-HIV Activity

  摘要：

  We have recently discovered that 6-aminoquinolone derivatives could be valid leads for the development of new anti-HIV agents because of their new and diversified mode of action. In fact, studies carried out on the lead WM5 showed that this derivative is able to inhibit the Tat-mediated long terminal repeat driven transcription, an essential step in the HIV-1 replication cycle. Thus, starting from lead WM5, we performed the design and synthesis of an enlarged series of 6-aminoquinolones, which permitted some very potent anti-HIV 6-amino derivatives to be obtained and the structure-activity relationship to be delineated. Some derivatives, 26c, 26e, 26i, and 26j, proved to be highly effective in inhibiting HIV replication at 50% inhibitory concentration in the range of 0.0087-0.7 mug/mL in MT-4, PBMCs and CEM cell lines coupled with positive selectivity indexes that reach values higher than 1000 on CEM cell lines for compounds 26e and 26i. Time-of-addition experiments clearly confirm that the new, potent 6-aminoquinolones interact at a postintegration step in the replication cycle of HIV.

  DOI：

  10.1021/jm049721p
• 作为产物：
  描述：

  2-巯基-5-氯苯并噻唑 在 氢氧化钾 、 四丁基溴化铵 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 1-(5-chloro-1,3-benzothiazol-2-yl)piperazine
  参考文献：
  名称：

  Structure Modifications of 6-Aminoquinolones with Potent Anti-HIV Activity

  摘要：

  We have recently discovered that 6-aminoquinolone derivatives could be valid leads for the development of new anti-HIV agents because of their new and diversified mode of action. In fact, studies carried out on the lead WM5 showed that this derivative is able to inhibit the Tat-mediated long terminal repeat driven transcription, an essential step in the HIV-1 replication cycle. Thus, starting from lead WM5, we performed the design and synthesis of an enlarged series of 6-aminoquinolones, which permitted some very potent anti-HIV 6-amino derivatives to be obtained and the structure-activity relationship to be delineated. Some derivatives, 26c, 26e, 26i, and 26j, proved to be highly effective in inhibiting HIV replication at 50% inhibitory concentration in the range of 0.0087-0.7 mug/mL in MT-4, PBMCs and CEM cell lines coupled with positive selectivity indexes that reach values higher than 1000 on CEM cell lines for compounds 26e and 26i. Time-of-addition experiments clearly confirm that the new, potent 6-aminoquinolones interact at a postintegration step in the replication cycle of HIV.

  DOI：

  10.1021/jm049721p

文献信息

• Phenyl-piperazine methanone derivatives, substituted by heterocyclic groups
  申请人：Jolidon Synese

  公开号：US20060128712A1

  公开（公告）日：2006-06-15

  The present invention relates to compounds of the general formula I wherein R 1 is the group and R 2 , R′, R″, R 3 , R 4 , R 5 , R 6 , R 7 , X 1 , X 1′ , X 2 , and N are as defined in the specification. Compounds of the invention are useful for the treatment of neurological and neuropsychiatric disorders.

  本发明涉及一般式I的化合物，其中R1是该基团，而R2、R′、R″、R3、R4、R5、R6、R7、X1、X1′、X2和N如规范中所定义。本发明的化合物对治疗神经和神经精神疾病有用。
• 1-, 3- and 8-substituted-9-deazaxanthines as potent and selective antagonists at the human A2B adenosine receptor
  作者：Angela Stefanachi、Jose Manuel Brea、Maria Isabel Cadavid、Nuria B. Centeno、Cristina Esteve、Maria Isabel Loza、Ana Martinez、Rosa Nieto、Enrique Raviña、Ferran Sanz

  DOI：10.1016/j.bmc.2008.01.002

  日期：2008.3.15

  A large series of piperazin-, piperidin- and tetrahydroisoquinolinamides of 4-(1,3-dialkyl-9-deazaxanthin-8-yl)phenoxyacetic acid were prepared through conventional or multiple parallel syntheses and evaluated for their binding affinity at the recombinant human adenosine receptors, chiefly at the hA(2B) and hA(2A) receptor subtypes. Several ligands endowed with high binding affinity at hA(2B) receptors, excellent selectivity over hA(2A) and hA(3) and a significant, but lower, selectivity over hA(1) were identified. Among them, piperazinamide derivatives 23 and 52, and piperidinamide derivative 69 proved highly potent at hA2B (K-i = 11, 2 and 5.5 nM, respectively) and selective towards hA(2A) (hA(2A)/hA(2B) SI = 912, 159 and 630, respectively), hA(3) (hA(3)/hA(2B) SI = > 100, 3090 and >180, respectively) and hA(1) (hA(1)/hA(2B) SI = > 100, 44 and 120, respectively), SI being the selectivity index. A number of selected ligands tested in functional assays in vitro showed very interesting antagonist activities and efficacies at both A(2A) and A(2B) receptor subtypes, with pA(2) values close to the corresponding pK(i)s. Structure-affinity and structure-selectivity relationships suggested that the binding potency at the hA(2B) receptor may be increased by lipophilic substituents at the N4-position of piperazinamides and that an ortho-methoxy substituent at the 8-phenyl ring and alkyl groups at NI larger than the ones at N3, in the 9-deazaxanthine ring, may strongly enhance the hA(2A)/hA(2B) SI. (C) 2008 Elsevier Ltd. All rights reserved.
• PHENYL-PIPERAZIN METHANONE DERIVATIVES
  申请人：F. Hoffmann-Roche AG

  公开号：EP1828154A1

  公开（公告）日：2007-09-05
• US7241761B2
  申请人：——

  公开号：US7241761B2

  公开（公告）日：2007-07-10
• US7429585B2
  申请人：——

  公开号：US7429585B2

  公开（公告）日：2008-09-30