2-oxo-2,3-dihydrobenzo[d]oxazole-5-sulfonamide | 31591-39-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: 2-oxo-2,3-dihydrobenzo[d]oxazole-5-sulfonamide
• 英文别名: 5-Sulfamidbenzoxazolon；2-oxo-2,3-dihydro-benzooxazole-5-sulfonic acid amide；2-oxo-3H-1,3-benzoxazole-5-sulfonamide
• CAS: 31591-39-6
• 化学式: C₇H₆N₂O₄S
• mdl: MFCD24388285
• 分子量: 214.202
• InChiKey: ZLNHEZVPPXSILS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-oxo-2,3-dihydrobenzo[d]oxazole-5-sulfonamide 在 盐酸 、 铜 、 四甲基氯化铵 、 potassium carbonate 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 4.33h， 生成 3-((1-(2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl)-1H-1,2,3-triazol-4-yl)methyl)-2-oxo-2,3-dihydrobenzo[d]oxazole-5-sulfonamide
  参考文献：
  名称：

  Azidothymidine “Clicked” into 1,2,3-Triazoles: First Report on Carbonic Anhydrase–Telomerase Dual-Hybrid Inhibitors

  摘要：

  Cancer cells rely on the enzyme telomerase (EC 2.7.7.49) to promote cellular immortality. Telomerase inhibitors (i.e., azidothymidine) can represent promising antitumor agents, although showing high toxicity when administered alone. Better outcomes were observed within a multipharmacological approach instead. In this context, we exploited the validated antitumor targets carbonic anhydrases (CAs; EC 4.2.1.1) IX and XII to attain the first proof of concept on CA-telomerase dual-hybrid inhibitors. Compounds 1b, 7h, 8b, and 11b showed good in vitro inhibition potency against the CAs IX and XII, with K-I values in the low nanomolar range, and strong antitelomerase activity in PC-3 and HT-29 cells (IC(50 )values ranging from 5.2 to 9.1 mu M). High-resolution X-ray crystallography on selected derivatives in the adduct with hCA II as a model study allowed to determine their binding modes and thus to set the structural determinants necessary for further development of compounds selectively targeting the tumoral cells.

  DOI：

  10.1021/acs.jmedchem.0c00636
• 作为产物：
  描述：

  光气 、 3-氨基-4-羟基苯磺酰胺 以 四氢呋喃 、 甲苯 为溶剂， 以83%的产率得到2-oxo-2,3-dihydrobenzo[d]oxazole-5-sulfonamide
  参考文献：
  名称：

  Azidothymidine “Clicked” into 1,2,3-Triazoles: First Report on Carbonic Anhydrase–Telomerase Dual-Hybrid Inhibitors

  摘要：

  Cancer cells rely on the enzyme telomerase (EC 2.7.7.49) to promote cellular immortality. Telomerase inhibitors (i.e., azidothymidine) can represent promising antitumor agents, although showing high toxicity when administered alone. Better outcomes were observed within a multipharmacological approach instead. In this context, we exploited the validated antitumor targets carbonic anhydrases (CAs; EC 4.2.1.1) IX and XII to attain the first proof of concept on CA-telomerase dual-hybrid inhibitors. Compounds 1b, 7h, 8b, and 11b showed good in vitro inhibition potency against the CAs IX and XII, with K-I values in the low nanomolar range, and strong antitelomerase activity in PC-3 and HT-29 cells (IC(50 )values ranging from 5.2 to 9.1 mu M). High-resolution X-ray crystallography on selected derivatives in the adduct with hCA II as a model study allowed to determine their binding modes and thus to set the structural determinants necessary for further development of compounds selectively targeting the tumoral cells.

  DOI：

  10.1021/acs.jmedchem.0c00636

文献信息

• Small Molecule Alkoxy Oriented Selectiveness on Human Carbonic Anhydrase II and IX Inhibition
  作者：Murat Bozdag、Lochlin Cravey、Jacob Combs、Anusha Kota、Robert McKenna、Andrea Angeli、Silvia Selleri、Fabrizio Carta、Claudiu T. Supuran

  DOI：10.1002/cmdc.202200148

  日期：2022.6.3

  Selectivity drivers: We report in-depth details about the binding modes of a series of alkoxy-containing ureido benzenesulfonamides within human carbonic anhydrase II and IX isoform mimics. These were used as orthosteric probes to decipher the structural determinants responsible for driving isoform selectivity.

  选择性驱动因素：我们报告了一系列含烷氧基脲基苯磺酰胺在人碳酸酐酶 II 和 IX 亚型模拟物中的结合模式的深入细节。这些被用作正构探针来破译负责驱动异构体选择性的结构决定因素。
• New Insights into Conformationally Restricted Carbonic Anhydrase Inhibitors
  作者：Jacob Combs、Murat Bozdag、Lochlin D. Cravey、Anusha Kota、Robert McKenna、Andrea Angeli、Fabrizio Carta、Claudiu T. Supuran

  DOI：10.3390/molecules28020890

  日期：——

  hydroxide-substituted benzenesulfonamides on the inhibition of human carbonic anhydrase (CA; EC 4.2.1.1) enzymes. These compounds were tested in vitro of CA II and CA IX, two physiologically important CA isoforms. The most potent inhibitory molecules against CA IX, 3g, 3h, and 3k, were studied to understand their binding modes via X-ray crystallography in adduct with CA II and CA IX-mimic. This research further

  本文报告了一项关于吡啶基官能团与氢氧根取代的苯磺酰胺联合使用对抑制人碳酸酐酶 (CA; EC 4.2.1.1) 酶的影响的调查。这些化合物在 CA II 和 CA IX（两种生理上重要的 CA 亚型）的体外进行了测试。对 CA IX、3g、3h 和 3k 的最有效抑制分子进行了研究，以通过 X 射线晶体学在与 CA II 和 CA IX 模拟物的加合物中了解它们的结合模式。这项研究进一步扩展了 CA 抑制剂领域，以更好地了解人类发现的同种型之间的配体选择性。
• Druckempfindliches oder wärmeempfindliches Aufzeichnungsmaterial
  申请人：CIBA-GEIGY AG

  公开号：EP0027913A2

  公开（公告）日：1981-05-06

  Ein druckempfindliches oder wärmeempfindliches Aufzeichnungsmaterial, welches in seinem farbbildenden System als Farbentwickler für den Farbbildner mindestens eine Verbindung der Formel enthält, worin der Ring Z einen heterocyclischen Rest darstellt, welcher benachbart zum Bindungskohlenstoffatom keine Ketogruppe aufweist, X die direkte Bindung -O-, -CHR-, -NR-, -CONR-, -SO2NR-, -NR1-CO-NR2-, -NR1-CS-NR2- oder -NR1-SO2-NR2-, R, R1 und R2 unabhängig voneinander Wasserstoff, unsubstituiertes oder durch Halogen, Cyano oder Niederalkoxy substituiertes Alkyl mit höchstens 12 Kohlenstoffatomen, Benzyl, Phenyl, oder durch Halogen, Methyl oder Methoxy substituiertes Benzyl oder Phenyl, Q Kohlenstoff oder einen unsubstituierten oder substituierten Kohlenwasserstoffrest, Y Halogen und m 1 bis 3 bedeuten. Die Gruppierung -Q-Ym ist vorzugsweise -C(Hal)3, worin Hal Halogen bedeutet.

  一种压敏或热敏记录材料，其显色体系中含有至少一种式如下的化合物作为显色剂 其中环 Z 代表杂环基，该杂环基与键合碳原子之间没有酮基，X 代表直接键-O-、-CHR-、-NR-、-CONR-、-SO2NR-、-NR1-CO-NR2-、-NR1-CS-NR2-或-NR1-SO2-NR2-，R、R1 和 R2 相互独立地代表氢、具有至多 12 个碳原子的未取代或卤素、氰基或低级烷氧基取代的烷基、苄基、苯基或卤素、甲基或甲氧基取代的苄基或苯基，Q 是碳或未取代或取代的烃基，Y 是卤素，m 是 1 至 3。 -Q-Ym的基团最好是-C(Hal)3，其中Hal是卤素。
• Preparation of 2,3,4,5-tetrahydro-1,2,4,triazine-3-ones
  作者：Kh. Lozanova、D. Simov、V. Kalcheva

  DOI：10.1007/bf00475374

  日期：1987.9
• LOZANOVA, X.;KALCHEVA, V., IZV. XIM., 21,(1988) N, S. 367-370
  作者：LOZANOVA, X.、KALCHEVA, V.

  DOI：——

  日期：——