3-chloro-phenylsulfonylacetonitrile | 685119-21-5

• 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: 3-chloro-phenylsulfonylacetonitrile
• 英文别名: 2-(3-Chlorophenyl)sulfonylacetonitrile
• CAS: 685119-21-5
• 化学式: C₈H₆ClNO₂S
• mdl: MFCD04110735
• 分子量: 215.66
• InChiKey: OUIOXVQENXOETD-UHFFFAOYSA-N

物化性质

• 沸点：
  436.7±45.0 °C(Predicted)
• 密度：
  1.409±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  66.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-chloro-phenylsulfonylacetonitrile 在 吡啶 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 sodium ethanolate 、 sodium carbonate 、 三氯氧磷 作用下， 以 乙二醇二甲醚 、 乙醇 、 水 为溶剂， 反应 3.08h， 生成 7-(2-Chlorophenyl)-10-(3-chlorophenyl)sulfonyl-5-thia-1,8,11,12-tetrazatricyclo[7.3.0.02,6]dodeca-2(6),3,7,9,11-pentaene
  参考文献：
  名称：

  Synthesis and biological evaluation of triazolothienopyrimidine derivatives as novel HIV-1 replication inhibitors

  摘要：

  We identified a novel class of triazolothienopyrimidine (TTPM) compounds as potent HIV-1 replication inhibitors during a high-throughput screening campaign that evaluated more than 200,000 compounds using a cell-based full replication assay. Herein, we report the optimization of the antiviral activity in a cell-based assay system leading to the discovery of aryl-substituted TTPM derivatives (38, 44, and 45), which exhibited significant inhibition of HIV-1 replication with acceptable safety margins. These novel and potent TTPMs could serve as leads for further development. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.134
• 作为产物：
  描述：

  3-氯苯磺酰氯 、 氯乙腈 在 碳酸氢钠 、 sodium sulfite 作用下， 以 水 为溶剂， 反应 0.83h， 生成 3-chloro-phenylsulfonylacetonitrile
  参考文献：
  名称：

  Synthesis and biological evaluation of triazolothienopyrimidine derivatives as novel HIV-1 replication inhibitors

  摘要：

  We identified a novel class of triazolothienopyrimidine (TTPM) compounds as potent HIV-1 replication inhibitors during a high-throughput screening campaign that evaluated more than 200,000 compounds using a cell-based full replication assay. Herein, we report the optimization of the antiviral activity in a cell-based assay system leading to the discovery of aryl-substituted TTPM derivatives (38, 44, and 45), which exhibited significant inhibition of HIV-1 replication with acceptable safety margins. These novel and potent TTPMs could serve as leads for further development. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.134

文献信息

• Synthesis and biological study of 3-(phenylsulfonyl)thieno[2,3-e][1,2,3]triazolo[1,5-a]pyrimidines as potent and selective serotonin 5-HT6 receptor antagonists
  作者：Alexandre V. Ivachtchenko、Elena S. Golovina、Madina G. Kadieva、Angela G. Koryakova、Sergiy M. Kovalenko、Oleg D. Mitkin、Ilya M. Okun、Irina M. Ravnyeyko、Sergey E. Tkachenko、Oleg V. Zaremba

  DOI：10.1016/j.bmc.2010.05.051

  日期：2010.7

  A number of 3-(phenylsulfonyl)thieno[2,3-e][1,2,3]triazolo[1,5-a]pyrimidines were prepared and their 5-HT6 receptor binding affinity and ability to inhibit the functional cellular responses to serotonin were evaluated. 3-[(3-Chlorophenyl)sulfonyl]-N-(tetrahydrofuran-2-ylmethyl)thieno[2,3-e][1,2,3]triazolo[1,5-a]pyrimidin-5-amine 25,26} appeared to be the most active in a functional assay (IC50 = 29

  制备了许多3-（苯磺酰基）噻吩并[2,3- e ] [1,2,3]三唑并[1,5- a ]嘧啶，它们与5-HT 6受体的结合亲和力和抑制细胞功能的能力评估对5-羟色胺的反应。3-[（3-氯苯基）磺酰基] -N-（四氢呋喃-2-基甲基）噻吩并[2,3- e ] [1,2,3]三唑并[1,5 - a ]嘧啶-5-胺2 5，26 }似乎是最活跃的在功能测定法（IC 50  = 29.0纳米）和3-（苯基磺酰基） - ñ - （2-噻吩甲基）噻吩并[2,3- ë ] [1,2,3]三唑并[1,5- a ]嘧啶-5-胺2 1，28 }表明，在5-HT的最大亲和力6受体放射性配体结合测定法（ķ我 = 1.7纳米）。对5-HT 2A和5-HT 2B受体亲和力的筛选显示3-（苯磺酰基）噻吩并[2,3- e ] [1,2,3]三唑并[1,5- a ]嘧啶是高度选择性的5- HT 6受体配体。
• Pyrazolopyrimidines and pyrazolotriazines with 5-HT6 receptor affinity
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0941994B1

  公开（公告）日：2003-05-14
• US6194410B1
  申请人：——

  公开号：US6194410B1

  公开（公告）日：2001-02-27
• Synthesis and biological evaluation of triazolothienopyrimidine derivatives as novel HIV-1 replication inhibitors
  作者：Junwon Kim、Jeongjin Kwon、Doohyun Lee、Suyeon Jo、Dong-Sik Park、Jihyun Choi、Eunjung Park、Jong Yeon Hwang、Yoonae Ko、Inhee Choi、Moon Kyeong Ju、JiYe Ahn、Junghwan Kim、Sung-Jun Han、Tae-Hee Kim、Jonathan Cechetto、Jiyoun Nam、Sujin Ahn、Peter Sommer、Michel Liuzzi、Zaesung No、Jinhwa Lee

  DOI：10.1016/j.bmcl.2012.10.134

  日期：2013.1

  We identified a novel class of triazolothienopyrimidine (TTPM) compounds as potent HIV-1 replication inhibitors during a high-throughput screening campaign that evaluated more than 200,000 compounds using a cell-based full replication assay. Herein, we report the optimization of the antiviral activity in a cell-based assay system leading to the discovery of aryl-substituted TTPM derivatives (38, 44, and 45), which exhibited significant inhibition of HIV-1 replication with acceptable safety margins. These novel and potent TTPMs could serve as leads for further development. (C) 2012 Elsevier Ltd. All rights reserved.