4-aminomethylbenzenesulfonyl fluoride hydrochloride | 33719-29-8

• 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: 4-aminomethylbenzenesulfonyl fluoride hydrochloride
• 英文别名: AMBSF；4-(Aminomethyl)benzene-1-sulfonyl fluoride hydrochloride；4-(aminomethyl)benzenesulfonyl fluoride;hydrochloride
• CAS: 33719-29-8
• 化学式: C₇H₈FNO₂S*ClH
• 分子量: 225.671
• InChiKey: OZJWTUBGBIZUQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.23
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  68.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-aminomethylbenzenesulfonyl fluoride hydrochloride 在 氢氟酸 、 苯甲醚 、 三乙胺 作用下， 以 乙腈 为溶剂， 生成 3--sulfamoyl-L-alanin
  参考文献：
  名称：

  Potential inhibitors of L-asparagine biosynthesis. 4. Substituted sulfonamide and sulfonylhydrazide analogs of L-asparagine

  摘要：

  Several N-substituted sulfonamides and N'-substituted sulfonylhydrazides have been prepared as sulfur analogues of L-asparagine with the potential of acting as inhibitors of L-asparagine synthetase (ASase, from Novikoff hepatoma). L-Cysteine was converted in known steps to N-carboxy-3-(sulfonylchloro)-L-alanine dibenzyl ester (1). Condensation of 1 with O-benzylhydroxylamine, p-(fluorosulfonyl)benzylamine, or monoethyl fumarylhydrazide (9), followed by deblocking with HF, gave 3-(hydroxysulfamoyl)-L-alanine (3a), 3-[p-(fluorosulfonylbenzyl)]sulfamoyl-L-alanine (3c), and 3-sulfo-L-alanine S-[2-[(E)-3-(ethoxycarbonyl)acryloyl]hydrazide] (3e), respectively. Similarly, 1 with 2-chloroethylamine and deblocking with H2-Pd gave 3-[(2-chloroethyl)sulfamoyl]-L-alanine (3b). tert-Butyl carbazate was allowed to react with 1 and the tert-butyl group was removed with HCl. The resulting sulfonylhydrazide 7 was condensed with p-(fluorosulfonyl)benzoyl chloride and then deblocked with HF to give 3-sulfo-L-alanine S-[2-[P-(fluorosulfonyl)benzoyl]hydrazide] (3d). The inhibition of ASase by 3a-e at 2 mM was 97, 0, 30, 43, and 37%, respectively, and 3a was competitive with L-aspartic acid. Neither 3a nor 3e was effective in increasing the life span of mice bearing P-388 lymphocytic leukemia.

  DOI：

  10.1021/jm00199a008
• 作为产物：
  描述：

  N-formamid 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 4-aminomethylbenzenesulfonyl fluoride hydrochloride
  参考文献：
  名称：

  酶促反应网络中稳健性和弹性的分子工程

  摘要：

  生命系统依靠复杂的化学反应网络来控制空间和时间中分子的浓度。尽管生物网络极其复杂，但仍有可能识别出导致双稳态或振荡等功能输出的网络基序。化学中最大的挑战之一是从化学反应中创造这样的功能。一个关键的限制是我们缺乏对分子结构如何影响化学反应网络动力学的了解，从而阻碍了网络设计的鲁棒性（即，在大参数空间中起作用）和弹性（即，达到其超出范围）。平衡函数迅速）。在这里，我们证明网络中单个反应的反应速率可以控制系统达到极限循环振荡的动力学，从而获得有关控制这些网络动态的关键参数的信息。我们设想这些原则将被纳入网络基序的设计中，使化学家能够开发“分子软件”以在化学系统中创建功能行为。

  DOI：

  10.1021/jacs.7b00632

文献信息

• Potential Antitumor Agents via Inhibitors of L-Asparagine Synthetase: Substituted Sulfonamides and Sulfonyl Hydrazides Related to Glutamine
  作者：Steven Brynes、Victor J. Fiorina、David A. Cooney、Harry A. Milman

  DOI：10.1002/jps.2600671115

  日期：1978.11

  synthesized as potential inhibitors of L-asparagine synthetase and subjected to screening as antitumor agents. Target amino acids were obtained by condensation of a blocked reactive sulfonyl chloride with the appropriate amine or hydrazide, followed by deblocking with hydrogen--palladium or liquid hydrogen fluoride--anisole. Neither the target compounds nor their protected precursors inhibited the enzyme

  合成了一系列与谷氨酰胺结构相关的化合物4-（取代的氨基磺酰基）-和4-（取代的肼磺酰基）-2-氨基丁酸，它们是L-天冬酰胺合成酶的潜在抑制剂，并经过筛选作为抗肿瘤剂。通过将封端的反应性磺酰氯与适当的胺或酰肼缩合，然后用氢-钯或液态氟化氢-茴香醚解封来获得目标氨基酸。目标化合物及其受保护的前体都不能抑制L5178Y / AR的酶或延长P-388淋巴细胞白血病小鼠的寿命。然而，DL-4，4'-二硫代双[2-（苄氧基羰基氨基）丁酸]，一种合成目标氨基酸的中间体，在10 mM时对L-天冬酰胺合成酶有90％的抑制作用。
• ANTI-SARS-COV-2-SPIKE GLYCOPROTEIN ANTIBODIES AND ANTIGEN-BINDING FRAGMENTS
  申请人：Regeneron Pharmaceuticals, Inc.

  公开号：EP3889177A1

  公开（公告）日：2021-10-06

  The present disclosure provides antibodies and antigen-binding fragments thereof that bind specifically to a coronavirus spike protein and methods of using such antibodies and fragments for treating or preventing viral infections (e.g., coronavirus infections).

  本公开提供了与冠状病毒尖峰蛋白特异性结合的抗体及其抗原结合片段，以及使用这种抗体和片段治疗或预防病毒感染（如冠状病毒感染）的方法。
• Anti-SARS-CoV-2-Spike glycoprotein antibodies and antigen-binding fragments
  申请人：Regeneron Pharmaceuticals, Inc.

  公开号：US10975139B1

  公开（公告）日：2021-04-13

  The present disclosure provides antibodies and antigen-binding fragments thereof that bind specifically to a coronavirus spike protein and methods of using such antibodies and fragments for treating or preventing viral infections (e.g., coronavirus infections).

  本公开提供了与冠状病毒尖峰蛋白特异性结合的抗体及其抗原结合片段，以及使用这种抗体和片段治疗或预防病毒感染（如冠状病毒感染）的方法。
• ANTI-TMPRSS2 ANTIBODIES AND ANTIGEN-BINDING FRAGMENTS
  申请人：Regeneron Pharmaceuticals, Inc.

  公开号：EP3638698A1

  公开（公告）日：2020-04-22
• Methods Of Identifying Subjects Having An Increased Risk Of Developing A Coronavirus Infection And Treatment Thereof
  申请人：Regeneron Pharmaceuticals, Inc.

  公开号：US20220177982A1

  公开（公告）日：2022-06-09

  Methods of treating subjects having a coronavirus infection, and methods of identifying subjects having an increased risk of a coronavirus infection are provided herein.