2-isopropyl-1,2-benzisothiazol-3(2H)-one 1,1-dioxide | 91950-12-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-isopropyl-1,2-benzisothiazol-3(2H)-one 1,1-dioxide
• 英文别名: N-isopropylsaccharin；N-isopropyl saccharin；2-isopropyl-1,1-dioxo-1,2-dihydro-1λ⁶-benzo[d]isothiazol-3-one；2-isopropyl-1,1-dioxo-1λ⁶-benz[d]isothiazol-3-one；2-Isopropyl-1,1-dioxo-1λ⁶-benz[d]isothiazol-3-on；N-Isopropyl-saccharin；1,1-Dioxo-2-propan-2-yl-1,2-benzothiazol-3-one
• CAS: 91950-12-8
• 化学式: C₁₀H₁₁NO₃S
• mdl: MFCD04373847
• 分子量: 225.268
• InChiKey: QNERCWAWQBNQQV-UHFFFAOYSA-N

物化性质

• 熔点：
  62-64 °C
• 沸点：
  374.4±25.0 °C(Predicted)
• 密度：
  1.367±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934100090

反应信息

• 作为反应物：
  描述：

  2-isopropyl-1,2-benzisothiazol-3(2H)-one 1,1-dioxide 在 potassium tert-butylate 、 乙酸酐 作用下， 反应 4.58h， 生成 Cyano-[2-isopropyl-1,1-dioxo-1,2-dihydro-1λ6-benzo[d]isothiazol-(3Z)-ylidene]-acetic acid ethyl ester
  参考文献：
  名称：

  Novel spirosuccinimides with incorporated isoindolone and benzisothiazole 1,1-dioxide moieties as aldose reductase inhibitors and antihyperglycemic agents

  摘要：

  Compounds from two novel series of spirosuccinimides were prepared. Analogs of series 2 possessed a spiro-fused isoindolone moiety while those of series 3 contained a spiro-fused benzisothiazole S,S-dioxide group. These compounds were evaluated as aldose reductase inhibitors (ARI) in vitro by their ability to inhibit glyceraldehyde reduction using a partially purified bovine lens aldose reductase preparation and in vivo as inhibitors of galactitol accumulation in the lens, sciatic nerve, and diaphragm of galactose-fed rats. Many members from the isoindolone series 2, particularly those containing an isoindolone N-methyl moiety, showed good in vitro and in vivo potency. The most potent member, the 6-chloro analog 32, was resolved, and aldose reductase activity was found to reside almost exclusively in the (+)-enantiomer. Compound 32 was approximately equipotent in the sciatic nerve of the galactose-fed rat to other cyclic imide ARI's of similar in vitro activity, namely sorbinil and ADN-138 and also to tolrestat, an acetic acid-based ARI (ED50's 4-8 mg/kg). Compounds from both series, 2 and 3, were also found to lower plasma glucose levels of genetically obese db/db and ob/ob mice with potency similar to that of ciglitazone. However, members from these series failed to lower insulin levels of the ob/ob mouse at the doses tested.

  DOI：

  10.1021/jm00102a016
• 作为产物：
  描述：

  N-isopropyl-2-methyl-benzenesulfonamide 在 chromium(VI) oxide 、 高碘酸 作用下， 以 乙腈 为溶剂， 反应 8.0h， 以20%的产率得到2-isopropyl-1,2-benzisothiazol-3(2H)-one 1,1-dioxide
  参考文献：
  名称：

  Oxidative cyclization of N-alkyl-o-methyl-arenesulfonamides to biologically important saccharin derivatives

  摘要：

  Various biologically important saccharin skeletons and their N-alkyl derivatives have been efficiently prepared by chromium(VI) oxide catalyzed H5IO6 oxidation of N-alkyl-o-methyl-arenesulfonamides in acetonitrile. N-tert-Butyl saccharin skeletons were easily prepared by H5IO6-CrO3 oxidation of N-tert-butyl-o-methyl arenesulfonamides in the presence of acetic anhydride. The method that furnished the novel fluoro and trifluoromethyl substituted saccharin skeletons is characterized by two steps, a simple work-up procedure, a single purification and good overall yields from substituted toluene derivatives. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.05.038

文献信息

• BIARYL PDE4 INHIBITORS FOR TREATING PULMONARY AND CARDIOVASCULAR DISORDERS
  申请人：Singh Jasbir

  公开号：US20090136473A1

  公开（公告）日：2009-05-28

  The present invention relates to a genus of biaryl compounds containing at least one further ring. The compounds are PDE4 inhibitors useful for the treatment and prevention of stroke, myocardial infarct and cardiovascular inflammatory diseases and disorders. The compounds have general formula Ia, Ib, Ic or Id: A particular embodiment is

  本发明涉及一类含有至少一个进一步环的联苯化合物的属。这些化合物是PDE4抑制剂，用于治疗和预防中风、心肌梗死和心血管炎症性疾病和紊乱。这些化合物具有一般式Ia、Ib、Ic或Id： 一个特定的实施例是
• SUBSTITUTED BENZOAZOLE PDE4 INHIBITORS FOR TREATING PULMONARY AND CARDIOVASCULAR DISORDERS
  申请人：Singh Jasbir

  公开号：US20090130076A1

  公开（公告）日：2009-05-21

  The invention relates to substituted benzothiazoles, benzoxazoles—and their counterparts having pyridine and pyrimidine rings replacing the benzene ring—that are PDE4 inhibitors useful for treating stroke, myocardial infarct, and cardiovascular inflammatory conditions, to pharmaceutical compositions comprising these compounds, and to methods for the treatment of stroke, myocardial infarct, and cardiovascular inflammatory conditions in a mammal. The compounds have general formula I: in which A and B are carbocycles or heterocycles. A particular embodiment is

  这项发明涉及替代苯并噻唑、苯并噁唑以及它们的对应物，其中吡啶和嘧啶环取代苯环，这些化合物是PDE4抑制剂，用于治疗中风、心肌梗死和心血管炎症病症，以及包含这些化合物的药物组合物，以及在哺乳动物中治疗中风、心肌梗死和心血管炎症病症的方法。这些化合物具有一般式I：其中A和B是碳环或杂环。一个特定的实施例是
• Sulfonamide Ligands Attained Through Opening of Saccharin Derivatives
  作者：Richard I. Robinson、Ross Fryatt、Claire Wilson、Simon Woodward

  DOI：10.1002/ejoc.200600508

  日期：2006.10

  iPr, Bn, (CH2)2SMe; R2 = Bn, iPr, CHPh2, CHMePh]. The (iPr,Bn) compound is crystallographically characterised. If both R1 and R2 are sterically congested then reaction of the amino alcohol with the saccharin surrogate 1,2-C6H4(CO2Me)(SO2NHR2) is required. The saccharin-derived alcohols are converted into the oxazolines 1,2-C6H4(R1-oxazoline)(SO2NHR2) (R1 = H, Bn, Me, iPr; R2 = Bn, CHPh2, nPr, iPr, tBu

  文献 N-烷基糖精（糖精-R2）在某些情况下已通过结晶学显示为 O-烷基化区域异构体（3 个结构）。真正的前一种物质在 101 °C 的二恶烷中与 (S)-H2NCHR1 OH 反应生成 1,2-C6H4(CONHCHR1 OH)(SO2NHR2) [R1 = H, Me, iPr, Bn, (CH2)2SMe; R2 = Bn、iPr、CHPh2、CHMePh]。(iPr,Bn) 化合物具有结晶学特征。如果 R1 和 R2 都是空间拥挤的，则需要氨基醇与糖精替代物 1,2- (CO2Me)(SO2NHR2) 的反应。糖精衍生的醇转化为恶唑啉 1,2- (R1-恶唑啉)(SO2NHR2)（R1 = H、Bn、Me、iPr；R2 = Bn、CHPh2、nPr、iPr、tBu、CHMePh）。二苄基化合物具有结晶学特征。(© Wiley-VCH Verlag GmbH & Co
• Novel benzenesulfonamide and 1,2-benzisothiazol-3(2H)-one-1,1-dioxide derivatives as potential selective COX-2 inhibitors
  作者：Ehab S. Taher、Tarek S. Ibrahim、Mohamed Fares、Amany M.M. AL-Mahmoudy、Abdullah F. Radwan、Khaled Y. Orabi、Osama I. El-Sabbagh

  DOI：10.1016/j.ejmech.2019.03.042

  日期：2019.6

  Two new series of 1,2-benzisothiazol-3(2H)-one-1,1-dioxide derivatives containing either five membered heterocyclic rings or aryl hydrazones were synthesized and evaluated for their in vitro COX-1/COX-2 inhibitory activity. In vivo anti-inflammatory evaluation revealed that benzenesulfonamides bearing pyrazole moiety 19, 20 and its cyclized form 23 exhibited the highest anti-inflammatory activity with

  合成了两个新的包含五个成员杂环或芳基的1,2-苯并噻唑-3（2 H）-one-1,1-二氧化物衍生物系列，并评估了它们的体外COX-1 / COX-2抑制活性。体内抗炎评价表明，苯磺酰胺类轴承吡唑部分19，20和其环化形式23具有相当的效力塞来昔布显示出最高的抗炎活性。此外，溃疡活性评价表明，化合物19，20和23与消炎痛作为参考药物相比，发挥了最小的溃疡指数。还对COX-2活性位点进行了对最具选择性的COX-2衍生物的对接研究。苯磺酰胺衍生物19和20在COX-2活性位点内部显示出更高的预测结合亲和力。分子模型模拟和药物相似性研究表明与所获得的生物学评价吻合良好。
• Regioselective Alkylation of Saccharin with Alcohols under Mitsunobu Conditions
  作者：Xiaolong Wang、Yanying Ma、Tingting Ju

  DOI：10.3184/174751913x13716447161975

  日期：2013.7

  The regioselective Mitsunobu alkylation of saccharin with various alcohols has been examined. The N/O-alkylation is dependent on the steric hindrance of the alcohols, that is, less sterically hindered alcohol preferentially afford N-alkylated saccharin and vice versa.

  已经研究了糖精与各种醇的区域选择性 Mitsunobu 烷基化。N/O-烷基化取决于醇的空间位阻，即空间位阻较小的醇优先提供N-烷基化糖精，反之亦然。