N-tert-butyl-4-bromomethylbenzenesulfonamide | 415679-05-9

• 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-tert-butyl-4-bromomethylbenzenesulfonamide
• 英文别名: 4-(bromomethyl)-N-tert-butylbenzenesulfonamide；4-bromomethyl-N-t-butylbenzenesulfonamide；4-Bromomethyl-N-t-butyl-benzenesulfonamide
• CAS: 415679-05-9
• 化学式: C₁₁H₁₆BrNO₂S
• 分子量: 306.224
• InChiKey: RJAHIBYGPYJWQJ-UHFFFAOYSA-N

物化性质

• 沸点：
  381.8±44.0 °C(Predicted)
• 密度：
  1.397±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-tert-butyl-4-bromomethylbenzenesulfonamide 在 四(三苯基膦)钯 、 ammonium acetate 、 溶剂黄146 、 三氟乙酸 、 锌 作用下， 以 乙二醇二甲醚 、 溶剂黄146 为溶剂， 生成 5-(4-aminosulfonylphenyl)-4-(5-chloro-2-thienyl)-2-methyloxazole
  参考文献：
  名称：

  4-Aryl/cycloalkyl-5-phenyloxazole derivatives as selective COX-2 inhibitors

  摘要：

  A series of 4-aryl/cycloalkyl-5-phenyloxazole derivatives was synthesized and evaluated for their ability to inhibit cyclooxygenase-2 (COX-2) and cyclooxygenase-1 (COX-1). These compounds were found to be potent and selective COX-2 inhibitors. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00670-9
• 作为产物：
  描述：

  对甲苯磺酰氯 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 生成 N-tert-butyl-4-bromomethylbenzenesulfonamide
  参考文献：
  名称：

  靶向多药理学：发现一种高效的非羟肟酸酯双重基质金属蛋白酶（MMP）-10 / -13抑制剂

  摘要：

  基质金属蛋白酶（MMP）在许多疾病（例如癌症，动脉粥样硬化或关节炎）中起关键作用。随着对生物途径基础网络知识的稳定增长，最近人们对MMP抑制的兴趣得到了振兴。基于对MMP网络中MMP-10和MMP-13的相关性的新见解以及对异羟肟酸酯抑制剂的临床开发禁止，发现针对特定MMP的非异羟肟酸酯多靶点药物尤为重要。在这里，我们公开了一种非常有效和选择性的非异羟肟酸酯MMP-10 / -13抑制剂的发现。高效能（IC 50 31 nM [MMP-10]和5 nM [MMP-13]的选择性和对MMP-1，-2，-3，-7，-8，-9，-12和-14的选择性使得该化合物能够破译引起疾病的MMP网络，并通过针对性的多药理学产生新的治疗选择。

  DOI：

  10.1021/acs.jmedchem.7b01001

文献信息

• DUAL-ACTING ANTIHYPERTENSIVE AGENTS
  申请人：Allegretti Paul

  公开号：US20090270473A1

  公开（公告）日：2009-10-29

  The invention relates to compounds having the formula: wherein: Q, W, Y, Z, r, and Ar are as defined in the specification, and pharmaceutically acceptable salts thereof. These compounds have AT 1 receptor antagonist activity and neprilysin inhibition activity. The invention is also directed to pharmaceutical compositions comprising such compounds; methods of using such compounds; and process and intermediates for preparing such compounds.

  这项发明涉及具有以下式的化合物：其中：Q、W、Y、Z、r 和 Ar 如规范中所定义，并其药学上可接受的盐。这些化合物具有AT1受体拮抗活性和酶抑制活性。该发明还涉及包含这些化合物的药物组合物；使用这些化合物的方法；以及制备这些化合物的过程和中间体。
• Synthesis of cinchonidinium salts containing sulfonamide functionalities and their catalytic activity in asymmetric alkylation reactions
  作者：Shinichi Itsuno、Shunya Yamamoto、Shohei Takata

  DOI：10.1016/j.tetlet.2014.09.052

  日期：2014.10

  Various kinds of 4-(bromomethyl)benzenesulfonamides were prepared as quaternization reagent of cinchonidine. Cinchonidinium salts obtained from the quaternization of cinchonidine with 4-(bromomethyl)benzenesulfonamide showed highly enantioselective catalytic activity in the asymmetric benzylation of N-(diphenylmethylene)glycine tert-butyl ester. The corresponding phenylalanine derivative was obtained

  制备了各种4-（溴甲基）苯磺酰胺作为辛可尼丁的季铵化试剂。由辛可尼丁与4-（溴甲基）苯磺酰胺的季铵化反应而得到的辛可宁鎓盐在N-（二苯基亚甲基）甘氨酸叔丁酯的不对称苄基化反应中表现出高度对映选择性的催化活性。以高收率和高对映选择性（高达98％ee）获得相应的苯丙氨酸衍生物。
• Dual-acting antihypertensive agents
  申请人：Theravance, Inc.

  公开号：US07989484B2

  公开（公告）日：2011-08-02

  The invention relates to compounds having the formula: wherein: Q, W, Y, Z, r, and Ar are as defined in the specification, and pharmaceutically acceptable salts thereof. These compounds have AT1 receptor antagonist activity and neprilysin inhibition activity. The invention is also directed to pharmaceutical compositions comprising such compounds; methods of using such compounds; and process and intermediates for preparing such compounds.

  本发明涉及具有以下式子的化合物：其中：Q，W，Y，Z，r和Ar如规范中所定义，并且其药学上可接受的盐。这些化合物具有AT1受体拮抗活性和神经肽酶抑制活性。本发明还涉及包含这些化合物的制药组合物，使用这些化合物的方法以及制备这些化合物的过程和中间体。
• Design, synthesis, and biological evaluation of 1,2,4-triazole bearing 5-substituted biphenyl-2-sulfonamide derivatives as potential antihypertensive candidates
  作者：Jie Liu、Qin Liu、Xue Yang、Shengtao Xu、Hengyuan Zhang、Renren Bai、Hequan Yao、Jieyun Jiang、Mingqin Shen、Xiaoming Wu、Jinyi Xu

  DOI：10.1016/j.bmc.2013.10.017

  日期：2013.12

  A series of novel 1,2,4-triazole bearing 5-substituted biphenyl-2-sulfonamide derivatives were designed and synthesized to develop new angiotensin II subtype 2 (AT(2)) receptor agonists as novel antihypertensive candidates. It was found that 14f (IC50 = 0.4 nM) and 15e (IC50 = 5.0 nM) displayed potent AT(2) receptor affinity and selectivity in binding assays. Biological evaluation in vivo suggested that 14f is obviously superior to that of reference drug losartan in RHRs, and meanwhile, 14f has no significant impact on heart rate. The interesting activities of these compounds may make them promising candidates as antihypertensive agents. (C) 2013 Elsevier Ltd. All rights reserved.
• 4-(4-Cycloalkyl/aryl-oxazol-5-yl)benzenesulfonamides as Selective Cyclooxygenase-2 Inhibitors:  Enhancement of the Selectivity by Introduction of a Fluorine Atom and Identification of a Potent, Highly Selective, and Orally Active COX-2 Inhibitor JTE-522
  作者：Hiromasa Hashimoto、Katsuaki Imamura、Jun-ichi Haruta、Korekiyo Wakitani

  DOI：10.1021/jm010484p

  日期：2002.3.1

  A series of 4-(4-cycloalkyl/aryl-oxazol-5-yl)benzenesulfonamide derivatives were synthesized and evaluated for their abilities to inhibit cyclooxygenase-2 (COX-2) and cyclooxygenase-1 (COX-1) enzymes. In this series, substituent effects at the ortho position to the sulfonamide group on the phenyl ring were examined. Most substituents reduced or lost both COX-2 and COX-1 activities. In contrast, introduction of a fluorine atom preserved COX-2 potency and notably increased COX-1/COX-2 selectivity. This work led to the identification of a potent, highly selective, and orally active COX-2 inhibitor JTE-522 [9d, 4-(4-cyclohexyl-2-methyloxazol-5-yl)2-fluorobenzenesulfonamide], which is currently in phase II clinical trials for the treatment of rheumatoid arthritis, osteoarthritis, and acute pain.