N-(4-(aminosulfonyl)phenyl)-4-methoxybenzamide | 330657-89-1

• 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-(4-(aminosulfonyl)phenyl)-4-methoxybenzamide
• 英文别名: p-anisoylaminobenzenesulfonamide；4-methoxy-N-(4-sulfamoylphenyl)benzamide
• CAS: 330657-89-1
• 化学式: C₁₄H₁₄N₂O₄S
• 分子量: 306.342
• InChiKey: YAVDRNUBULTYQF-UHFFFAOYSA-N

物化性质

• 密度：
  1.384±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  N-(4-(aminosulfonyl)phenyl)-4-methoxybenzamide 在 sodium azide 、 四氯化硅 作用下， 以 乙腈 为溶剂， 反应 72.0h， 以100%的产率得到1-(4-(aminosulfonyl)phenyl)-5-(4-methoxyphenyl)-1H-tetrazole
  参考文献：
  名称：

  对接研究和两种四唑衍生物的晶体结构：5-(4-氯苯基)-1-{4-(甲基磺酰基)苯基}-1H-四唑和4-{5-(4-甲氧基苯基)-1H-四唑-1 -基}苯磺酰胺

  摘要：

  摘要 5-(4-氯苯基)-1-{4-(甲基磺酰基)苯基}-1H-四唑(3)和4-{5-(4-甲氧基苯基)-1H-四唑-1-基}苯磺酰胺的结构(5)已通过X射线晶体学测定。四唑 3 和 5 分别在单斜空间群 Ia 和 P21/c 中结晶。唑 3 的细胞尺寸为 a = 11.0413 (5) A, b = 11.8428 (5) A, c = 12.2483 (5) A3, β = 111.7129 (4)°, V = 1487.95 (11) A3, and Z = 4. 将其结构细化为 R1 = 0.0254（对于 3429 个观察到的反射 [I ≥ 2σ(I)]）和 wR2 = 0.0651（对于所有 3300 个唯一反射）。唑 5 的细胞尺寸为 a = 17.112 (3) A, b = 6.5904 (10) A, c = 12.935 (2) A3, β = 93.1981 (19)°

  DOI：

  10.1016/j.molstruc.2015.08.025
• 作为产物：
  描述：

  大茴香酸 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 N-(4-(aminosulfonyl)phenyl)-4-methoxybenzamide
  参考文献：
  名称：

  Novel 5-substituted 1H-tetrazoles as cyclooxygenase-2 (COX-2) inhibitors

  摘要：

  A series of novel 5-substituted 1H-tetrazoles as cyclooxygenase-2 (COX-2) inhibitors was prepared via treatment of various diaryl amides with tetrachlorosilane/sodium azide. All compounds were tested in cyclooxygenase (COX) assays in vitro to determine COX-1 and COX-2 inhibitory potency and selectivity. Tetrazoles contained a methylsulfonyl or sulfonamide group as COX-2 pharmacophore displayed only low inhibitory potency towards COX-2. Most potent compounds showed IC50 values of 6 and 7 mu M for COX-2. All compounds showed IC50 values greater 100 mu M for COX-1 inhibition. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.093

文献信息

• [EN] REMODILINS FOR AIRWAY REMODELING AND ORGAN FIBROSIS<br/>[FR] REMODILINES POUR LE REMODELAGE DES VOIES RESPIRATOIRES ET FIBROSE D'ORGANE
  申请人：UNIV CHICAGO

  公开号：WO2020206109A1

  公开（公告）日：2020-10-08

  Disclosed herein is a class of molecules termed remodilins that are effective in treating asthma, pulmonary fibrosis, and associated disorders. The molecules ameliorate asthma and pulmonary fibrosis symptoms by various mechanisms, including inhibiting airway smooth muscle contractile protein accumulation, reducing airway constrictor hyperresponsiveness, inhibiting bronchial fibroblast transformation into myofibroblasts, and/or treating or preventing airway or pulmonary fibrosis.

  本文披露了一类分子，称为remodilins，它们在治疗哮喘、肺纤维化及相关疾病方面具有有效性。这些分子通过各种机制改善哮喘和肺纤维化症状，包括抑制气道平滑肌收缩蛋白的积累，减少气道收缩过度反应，抑制支气管成纤维细胞向肌成纤维细胞的转化，和/或治疗或预防气道或肺纤维化。
• [EN] REMODILINS TO PREVENT OR TREAT CANCER METASTASIS, GLAUCOMA, AND HYPOXIA<br/>[FR] REMODILINES POUR PRÉVENIR OU TRAITER DES MÉTASTASES CANCÉREUSES, LE GLAUCOME ET L'HYPOXIE
  申请人：UNIV CHICAGO

  公开号：WO2020206118A1

  公开（公告）日：2020-10-08

  Disclosed herein is a class of molecules termed remodilins that inhibit serum response factor (SRF). By inhibiting SRF, a number of downstream pathways can be targeted. The remodilins can be used to treat glaucoma, inhibit tumor cell growth, inhibit tumor metastasis, inhibit hypoxia-induced response, and/or reduce cellular metabolism.

  本文披露了一类分子，被称为抑制血清反应因子（SRF）的remodilins。通过抑制SRF，可以针对许多下游途径。Remodilins可用于治疗青光眼，抑制肿瘤细胞生长，抑制肿瘤转移，抑制缺氧诱导反应，和/或减少细胞代谢。
• US4025508A
  申请人：——

  公开号：US4025508A

  公开（公告）日：1977-05-24
• Novel 5-substituted 1H-tetrazoles as cyclooxygenase-2 (COX-2) inhibitors
  作者：Baker Jawabrah Al-Hourani、Sai Kiran Sharma、Mavanur Suresh、Frank Wuest

  DOI：10.1016/j.bmcl.2012.01.093

  日期：2012.3

  A series of novel 5-substituted 1H-tetrazoles as cyclooxygenase-2 (COX-2) inhibitors was prepared via treatment of various diaryl amides with tetrachlorosilane/sodium azide. All compounds were tested in cyclooxygenase (COX) assays in vitro to determine COX-1 and COX-2 inhibitory potency and selectivity. Tetrazoles contained a methylsulfonyl or sulfonamide group as COX-2 pharmacophore displayed only low inhibitory potency towards COX-2. Most potent compounds showed IC50 values of 6 and 7 mu M for COX-2. All compounds showed IC50 values greater 100 mu M for COX-1 inhibition. (C) 2012 Elsevier Ltd. All rights reserved.
• Docking studies and the crystal structure of two tetrazole derivatives: 5-(4-chlorophenyl)-1-{4-(methylsulfonyl)phenyl}-1H-tetrazole and 4-{5-(4-methoxyphenyl)-1H-tetrazol-1-yl}benzenesulfonamide
  作者：Baker Jawabrah Al-Hourani、Musa I. El-Barghouthi、Robert Mcdonald、Wajdy Al-Awaida、Frank Wuest

  DOI：10.1016/j.molstruc.2015.08.025

  日期：2015.12

  Abstract The structures of 5-(4-chlorophenyl)-1-4-(methylsulfonyl)phenyl}-1H-tetrazole (3) and 4-5-(4-methoxyphenyl)-1H-tetrazol-1-yl}benzenesulfonamide (5) have been determined by X-ray crystallography. Tetrazoles 3 and 5 crystallize in the monoclinic space groups Ia and P21/c, respectively. The cell dimensions of azole 3 are a = 11.0413 (5) A, b = 11.8428 (5) A, c = 12.2483 (5) A3, β = 111.7129

  摘要 5-(4-氯苯基)-1-4-(甲基磺酰基)苯基}-1H-四唑(3)和4-5-(4-甲氧基苯基)-1H-四唑-1-基}苯磺酰胺的结构(5)已通过X射线晶体学测定。四唑 3 和 5 分别在单斜空间群 Ia 和 P21/c 中结晶。唑 3 的细胞尺寸为 a = 11.0413 (5) A, b = 11.8428 (5) A, c = 12.2483 (5) A3, β = 111.7129 (4)°, V = 1487.95 (11) A3, and Z = 4. 将其结构细化为 R1 = 0.0254（对于 3429 个观察到的反射 [I ≥ 2σ(I)]）和 wR2 = 0.0651（对于所有 3300 个唯一反射）。唑 5 的细胞尺寸为 a = 17.112 (3) A, b = 6.5904 (10) A, c = 12.935 (2) A3, β = 93.1981 (19)°