苯唑拉胺 | 3368-13-6

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 苯唑拉胺
• 英文名称: benzolamide
• 英文别名: BZA；5-benzenesulfonamido-1,3,4-thiadiazol-2-sulfonamide；5-(benzenesulfonamido)-1,3,4-thiadiazole-2-sulfonamide
• CAS: 3368-13-6
• 化学式: C₈H₈N₄O₄S₃
• 分子量: 320.374
• InChiKey: PWDGTQXZLNDOKS-UHFFFAOYSA-N

物化性质

• 熔点：
  239.5°C (rough estimate)
• 沸点：
  585.9±33.0 °C(Predicted)
• 密度：
  1.6772 (rough estimate)
• 溶解度：
  DMSO：250 mg/mL（780.35 mM；需要超声）

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  177
• 氢给体数：
  2
• 氢受体数：
  9

安全信息

• 海关编码：
  2935009090
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  copper(II) perchlorate hexahydrate 、 苯唑拉胺 、 氨 以 乙醇 为溶剂， 生成
  参考文献：
  名称：

  Copper complexes modelling the interaction between benzolamide and Cu-substituted carbonic anhydrase. Crystal structure of Cu(bz)(NH3)4 complex

  摘要：

  New copper benzolamide (H(2)bz, 5-phenylsulfonamide-1,3,4-thiadiazole-2-sulfonamide) complexes with ammonia, diethylentriamine (dien) and dipropylentriamine (dipn) have been prepared. The complex [Cu(bz)(NH3)(4)] crystallises in the monoclinic space group P2(1)/n with a = 7.621(3), b = 19.91(5), c = 11.291(3) Angstrom, beta = 93.17(4)degrees and Z = 4. The Cu(II) is five-coordinated with an almost regular square pyramidal geometry. The dideprotonated sulfonamide behaves as monodentate ligand interacting with the metal ion through the N atom of the unsubstituted sulfonamide group. In the EPR spectrum, exchange coupling between Cu(II) polyhedra of different orientations in the unit cell is observed. The dien and dipn ligands provide a model of the histidine environment of the metal ion in carbonic anhydrase (CA). From the spectroscopic properties, the ternary triamine complexes can be considered as analogous of the adducts formed by Cu-CA and the inhibitor benzolamide. (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0020-1693(97)06020-9
• 作为产物：
  描述：

  5-氨基-1,3,4-噻二唑-2-磺酰胺 、 苯磺酰氯 在 sodium hydroxide 作用下， 以 水 、 丙酮 为溶剂， 以15.5%的产率得到苯唑拉胺
  参考文献：
  名称：

  新型碳酸酐酶抑制剂的合成与评价

  摘要：

  合成了一系列新的磺酰胺衍生物，其结构经1 H NMR和ESI-MS确证。用Dock6的工具评估了一些目标化合物，并研究了所有新化合物对碳酸酐酶II的抑制作用。另外，已经研究了某些化合物在小鼠中的抗缺氧作用。结果表明，九种目标化合物表现出与乙酰唑酰胺一样有效的效果，而十种化合物对碳酸酐酶II的抑制作用比乙酰唑酰胺更强。其中三个（I-8，I-18和I'-3）可以明显延长缺氧小鼠的存活时间，值得进一步研究。

  DOI：

  10.1016/j.bmc.2011.03.061

文献信息

• Direct sulfonylamidation of unfunctionalized arenes in C H activation manner: A simple protocol to access primary sulfonamides
  作者：Satyanarayana Tummanapalli、Srinu Bodige、Kali Charan Gulipalli、Srinivas Endoori、Srinivas Medaboina、Kalyani Mallidi

  DOI：10.1016/j.tetlet.2022.153781

  日期：2022.5

  thiols by harsh oxidation conditions or chlorination of sulfonic acids. We herein report a simple and convenient protocol to access primary sulfonamides by direct sulfonylamidation of unfunctionalized arenes [direct CH activation to C-SO2NH2]. Usefulness of the protocol has been further demonstrated successfully by extending the application to formal syntheses of known drugs, acetazolamide (2), methazolamide

  在所有具有生物活性的磺胺类药物中，具有末端SO 2 NH 2基团的伯磺胺类药物由于其高锌结合能力而占有特殊的地位，已成功地用于发现几种不同的药用活性伯磺胺类药物。然而，大多数初级磺酰胺合成涉及用磺酰氯处理氨的传统方法，而磺酰氯通常是通过苛刻的氧化条件或氯化磺酸从硫醇中获得的。我们在此报告了一种简单方便的方案，通过对未官能化芳烃的直接磺酰酰胺化[直接 C H 活化为 C-SO 2 NH 2来获得初级磺酰胺]。通过将应用扩展到已知药物、乙酰唑胺 (2)、methazolamide (3)、ethoxzolamide (4) 和药理活性苯甲酰胺 (6) 的正式合成，进一步成功地证明了该协议的有用性。
• Ophthalmic compositions comprising combinations of carbonic anhydrase inhibitors and S-(-)-1-(tert-butylamino)-3-(4-morpholino-1,2,5-thiadiazol-3-yl)-oxy-2-propanol for topical application in the treatment of elevated intraocular pressure
  申请人：Merck & Co., Inc.

  公开号：EP0014642A2

  公开（公告）日：1980-08-20

  Although carbonic anhydrase inhibitors (C.A.l) can be administered systemically by oral or intravenous routes, attempts to administer them topically have been ineffective and inactive in the treatment of intraocular hypertension. The alkali metal salts, especially the sodium and potassium salts, of salt-forming carbonic anhydrase inhibitors in combination with S-(-)-1- (tert-butylamino) -3-[(4-morpholino-1,2,5-thiadiazol -3-yl)oxy] -2-propanol or its racemic modification are now found to be remarkably effective in lowering intraocular pressure, even in normotensive hosts, but especially in those hosts having an elevated intraocular pressure.

  虽然碳酸酐酶抑制剂（C.A.l）可以通过口服或静脉注射的方式进行全身给药，但在治疗眼内高压方面，局部给药的尝试一直效果不佳，而且没有活性。现在发现，成盐碳酸酐酶抑制剂的碱金属盐，特别是钠盐和钾盐，与 S-(-)-1-（叔丁基氨基）-3-[（4-吗啉基-1,2,5-噻二唑-3-基）氧基] -2-丙醇或其外消旋体结合使用，对降低眼内压非常有效，即使对正常血压的宿主也是如此，尤其是对眼内压升高的宿主。
• Ophthalmic compositions of carbonic anhydrase inhibitors for topical application in the treatment of elevated intraocular pressure
  申请人：Merck & Co., Inc.

  公开号：EP0036351A2

  公开（公告）日：1981-09-23

  Although dibasic carbonic anhydrase inhibitors (CAI.) can be administered systemically by oral or intravenous routes, attempts to administer them topically were inadvisable because of their elevated pH. The mono-alkali metal salts in the treatment of intraocular hypertension especially the sodium and potassium salts, of dibasic salt-forming C.A.I. are as effective in lowering intraocular pressure as dialkali metal salts of dibasic C.A.I. while having a pH more in harmony with ocular pH. They are found particularly useful when administered in conjunction with an ophthalmologically acceptable water-soluble polymer such as hydroxypropylcellulose in an aqueous carrier.

  虽然二盐基碳酸酐酶抑制剂（CAI.）可通过口服或静脉注射途径进行全身给药，但由于其 pH 值升高，因此不宜尝试局部给药。治疗眼内高压的单碱金属盐，特别是二盐型 C.A.I. 的钠盐和钾盐，在降低眼内压方面的效果与二盐型 C.A.I. 的二碱金属盐相同，但 pH 值与眼内 pH 值更为协调。当它们与眼科可接受的水溶性聚合物（如水性载体中的羟丙基纤维素）一起使用时，效果尤为显著。
• Ophthalmic inserts for lowering intraocular pressure comprising carbonic anhydrase inhibitors
  申请人：Merck & Co., Inc.

  公开号：EP0033042A1

  公开（公告）日：1981-08-05

  Although carbonic anhydrase inhibitors (C.A.I.) can be administered systemically by oral or intravenous routes, attempts to administer them topically have been ineffective and inactive in the treatment of intraocular hypertension. The alkali metal salts, especially the sodium and potassium salts, of salt-forming C.A.I. are now found to be remarkably effective in lowering intraocular pressure, even in normotensive hosts, but especially in those hosts having an elevated intraocular pressure.

  虽然碳酸酐酶抑制剂（C.A.I.）可以通过口服或静脉注射的方式进行全身给药，但在治疗眼内高压方面，局部给药的尝试一直无效，且效果不佳。现在发现，成盐的 C.A.I. 的碱金属盐，特别是钠盐和钾盐，对降低眼内压非常有效，即使对正常血压的宿主也是如此，尤其是对眼内压升高的宿主。
• Notes - Heterocyclic Sulfonamides as Carbonic Anhydrase Inhibitors. 2-Acylamido- and 2-Sulfonamido-1,3,4-thiadiazole-5-sulfonamides
  作者：J. Vaughan, Jr.、J. Eichler、G. Anderson

  DOI：10.1021/jo01112a612

  日期：1956.6