N-[4-(isocyanato)phenylsulfonyl]morpholine | 790691-28-0

• 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: N-[4-(isocyanato)phenylsulfonyl]morpholine
• 英文别名: 4-(4-Isocyanatophenyl)sulfonylmorpholine
• CAS: 790691-28-0
• 化学式: C₁₁H₁₂N₂O₄S
• 分子量: 268.293
• InChiKey: LMVXTQKAYBAGNN-UHFFFAOYSA-N

物化性质

• 沸点：
  422.5±55.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  84.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-[4-(isocyanato)phenylsulfonyl]morpholine 在 盐酸 、 TEA 作用下， 以 1,4-二氧六环 为溶剂， 反应 19.0h， 生成 1-deoxy-1-[6-[[[(4-(morpholin-1-ylsulfonyl)phenyl)amino]carbonyl]amino]-9H-purin-9-yl]-N-ethyl-β-D-ribofuranuronamide
  参考文献：
  名称：

  新型N6- [4-（取代）磺酰胺基苯基氨基甲酰基]腺苷-5'-尿酰胺作为A3腺苷受体激动剂的合成及生物学评价。

  摘要：

  一系列新的1-脱氧-1-[[（6-（4-（取代-氨基磺酰基）苯基）氨基）羰基氨基-9H-嘌呤-9-基] -N-乙基-β-D-核呋喃核糖酰胺（83-102 ）已合成并在人A3腺苷受体亚型上进行了测试。这项工作中描述的所有衍生物在纳摩尔范围内均表现出与该受体的亲和力，与A1腺苷受体亚型相比具有良好的选择性，证实了对p-磺酰胺基部分对分子的活性有积极影响。发现磺酰胺基核上的最佳取代基是小的烷基，如甲基，异丙基，乙基或烯丙基部分（化合物96-100），而氨基上的单取代导致A3亲和力值降低。当磺酰胺基核心中的氨基由氢化杂环如哌啶，吗啉或吡咯啉表示时，相对于A1腺苷受体亚型的选择性增加。诸如金刚烷和具有四个以上碳原子的烷基链之类的大基团不利于本文所述的A3腺苷受体激动剂的亲和力和选择性。

  DOI：

  10.1021/jm0408161
• 作为产物：
  描述：

  对硝基苯磺酰氯 在 溶剂黄146 、 三乙胺 、 N,N-二异丙基乙胺 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 N-[4-(isocyanato)phenylsulfonyl]morpholine
  参考文献：
  名称：

  1,2-Benzisothiazol-3-one derivatives as a novel class of small-molecule caspase-3 inhibitors

  摘要：

  A novel series of 1,2-benzisothiazol-3-one derivatives was synthesized and their biological activities were evaluated for inhibiting caspase-3 and -7 activities, in which some of them showed low nanomolar potency against caspase-3 in vitro and significant protection against apoptosis in a camptothecin-induced Jurkat T cells system. Among the tested compounds, compound 5i exhibited the most potent caspase-3 inhibitory activity (IC50 = 1.15 nM). The molecular docking predicted the interactions and binding modes of the synthesized inhibitor in the caspase-3 active site. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.03.002

文献信息

• Novel adenosine A3 receptor agonists
  申请人：Baraldi Giovanni Pier

  公开号：US20050250729A1

  公开（公告）日：2005-11-10

  The compounds of the following formula: wherein Ar, R and R 1 have the meanings given in the specification. This series of sulfonamido derivatives with a conserved uronamide group at the 5′ position provide superior A3 receptor affinity as well as selectivity. These new adenosine agonists are sulfonamido derivatives N-substituted with aliphatic groups (cyclic or linear) or aromatic radicals.

  以下化合物的公式：其中Ar，R和R1具有规范中给出的含义。这一系列的磺酰胺衍生物在5'位置具有保守的糖醛酰胺基团，提供了优越的A3受体亲和力和选择性。这些新的腺苷受体激动剂是磺酰胺衍生物，其N-取代基为脂肪基（环状或线性）或芳香基团。
• NOVEL ADENOSINE A3 RECEPTOR AGONISTS
  申请人：Baraldi Pier Giovanni

  公开号：US20090233878A1

  公开（公告）日：2009-09-17

  The present invention provides compounds of the formula wherein Ar, R and R 1 have a meaning as defined herein in the specification. Compounds of formula (I) are agonists of the A 3 adenosine receptor and, thus, may be employed for the treatment of conditions mediated by the A 3 adenosine receptor. Accordingly, the compounds of formula (I) may be employed for treatment of behavioral depression, cerebral ischemia, hypotension, chemically induced seizures, inflammatory diseases, asthma, and cancer diseases expressing the adenosine A 3 receptor.

  本发明提供了具有以下公式的化合物，其中Ar，R和R1的含义如本说明书中所定义。公式（I）的化合物是A3腺苷受体的激动剂，因此可用于治疗由A3腺苷受体介导的疾病。因此，公式（I）的化合物可用于治疗行为性抑郁症，脑缺血，低血压，化学诱导的癫痫，炎症性疾病，哮喘和表达腺苷A3受体的癌症疾病。
• US7511133B2
  申请人：——

  公开号：US7511133B2

  公开（公告）日：2009-03-31
• 1,2-Benzisothiazol-3-one derivatives as a novel class of small-molecule caspase-3 inhibitors
  作者：Lixin Wu、Meiqi Lu、Zhihui Yan、Xiaobin Tang、Bo Sun、Wei Liu、Honggang Zhou、Cheng Yang

  DOI：10.1016/j.bmc.2014.03.002

  日期：2014.4

  A novel series of 1,2-benzisothiazol-3-one derivatives was synthesized and their biological activities were evaluated for inhibiting caspase-3 and -7 activities, in which some of them showed low nanomolar potency against caspase-3 in vitro and significant protection against apoptosis in a camptothecin-induced Jurkat T cells system. Among the tested compounds, compound 5i exhibited the most potent caspase-3 inhibitory activity (IC50 = 1.15 nM). The molecular docking predicted the interactions and binding modes of the synthesized inhibitor in the caspase-3 active site. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis and Biological Evaluation of Novel <i>N</i>⁶-[4-(Substituted)sulfonamidophenylcarbamoyl]adenosine-5‘-uronamides as A₃ Adenosine Receptor Agonists
  作者：Pier Giovanni Baraldi、Francesca Fruttarolo、Mojgan Aghazadeh Tabrizi、Romeo Romagnoli、Delia Preti、Andrea Bovero、Maria Josè Pineda de Las Infantas、Allan Moorman、Katia Varani、Pier Andrea Borea

  DOI：10.1021/jm0408161

  日期：2004.10.1

  H-purin-9 -yl]-N-ethyl-beta-D-ribofuranuronamides (83-102) have been synthesized and tested at the human A3 adenosine receptor subtype. All the derivatives described in this work displayed affinity versus this receptor in the nanomolar range and good selectivity versus A1 adenosine receptor subtype, confirming that the p-sulfonamido moiety positively affected the activity of the molecules. The best

  一系列新的1-脱氧-1-[[（6-（4-（取代-氨基磺酰基）苯基）氨基）羰基氨基-9H-嘌呤-9-基] -N-乙基-β-D-核呋喃核糖酰胺（83-102 ）已合成并在人A3腺苷受体亚型上进行了测试。这项工作中描述的所有衍生物在纳摩尔范围内均表现出与该受体的亲和力，与A1腺苷受体亚型相比具有良好的选择性，证实了对p-磺酰胺基部分对分子的活性有积极影响。发现磺酰胺基核上的最佳取代基是小的烷基，如甲基，异丙基，乙基或烯丙基部分（化合物96-100），而氨基上的单取代导致A3亲和力值降低。当磺酰胺基核心中的氨基由氢化杂环如哌啶，吗啉或吡咯啉表示时，相对于A1腺苷受体亚型的选择性增加。诸如金刚烷和具有四个以上碳原子的烷基链之类的大基团不利于本文所述的A3腺苷受体激动剂的亲和力和选择性。