3-硝基-联苯-4-磺酰氯 | 101366-50-1

• 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: 3-硝基-联苯-4-磺酰氯
• 英文名称: 3'-nitrobiphenyl-4-sulfonyl chloride
• 英文别名: 4-(3-nitrophenyl)benzenesulfonyl chloride
• CAS: 101366-50-1
• 化学式: C₁₂H₈ClNO₄S
• 分子量: 297.719
• InChiKey: KTXDVWDRGRWSJW-UHFFFAOYSA-N

物化性质

• 沸点：
  446.8±38.0 °C(Predicted)
• 密度：
  1.464±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  88.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-硝基-联苯-4-磺酰氯 在 钯 吡啶 、 氢气 作用下， 以 乙醇 为溶剂， 95.0 ℃ 、101.33 kPa 条件下， 反应 21.0h， 生成 3''-Amino-biphenyl-4-sulfonic acid (2-phenyl-2H-pyrazol-3-yl)-amide
  参考文献：
  名称：

  Synthesis of Sulfaphenazole Derivatives and Their Use as Inhibitors and Tools for Comparing the Active Sites of Human Liver Cytochromes P450 of the 2C Subfamily

  摘要：

  Twenty-three new derivatives of sulfaphenazole (SPA) were synthesized to further explore the topology of the active sites of human liver cytochromes P450 of the 2C subfamily and to find new selective inhibitors of these cytochromes. These compounds are derived from SPA by replacement of the NH2 and H (of the SO2NH function) substituents of SPA with various R-1 and R-2 groups, respectively. Their inhibitory effects were studied on recombinant CYP 2C8, 2C9, 2C18, and 2C19 expressed in yeast. High affinities for CYP 2C9 (IC50 < 1 muM) were only observed for SPA derivatives having the SO2NH function and a relatively small R-1 substituent (R-1 = NH2, CH3). Any increase in the size of R-1 led to a moderate decrease of the affinity, and the N-alkylation of the SO2NH function of SPA to a greater decrease of this affinity. The same structural changes led to opposite effects on molecular recognition by CYP 2C8 and 2C18, which generally exhibited similar behaviors. Thus, contrary to CYP 2C9, CYP 2C8 and 2C18 generally prefer neutral compounds with relatively large R-1 and R2 substituents. CYP 2C19 showed an even lower affinity for anionic compounds than CYP 2C8 and 2C18. However, as CYP 2C8 and 2C18, CYP 2C19 showed a much better affinity for neutral compounds derived ftom N-alkylation of SPA and for anionic compounds bearing a larger R, substituent. One of the new compounds (R-1 = methyl, R-2 = propyl) inhibited all human CYP 2Cs with IC50 values between 10 and 20 muM, while another one (R-1 = allyl, R-2 = methyl) inhibited all CYP 2Cs except CYP 2C9, and a third one (R-1 = R-2 = methyl) inhibited all CYP 2Cs except CYP 2C8. Only 2 compounds of the 25 tested derivatives were highly selective toward one human CYP 2C; these are SPA and compound I (Ri = CH3, R2 = H), which acted as selective CYP 2C9 inhibitors. However, some SPA derivatives selectively inhibited CYP 2C8 and 2C18. Since CYP 2C18 is hardly detectable in human liver, these derivatives could be interesting molecules to selectively inhibit CYP 2C8 in human liver microsomes. Thus, compound 11 (R-1 = NH2, R-2 = (CH2)(2)CH(CH3)(2)) appears to be particularly interesting for that purpose as its IC50 value for CYP 2C8 is low (3 muM) and 20-fold smaller than those found for CYP 2C9 and 2C19.

  DOI：

  10.1021/jm010861y
• 作为产物：
  描述：

  3-硝基联苯 在 氯磺酸 作用下， 反应 1.0h， 以65%的产率得到3-硝基-联苯-4-磺酰氯
  参考文献：
  名称：

  Synthesis of Sulfaphenazole Derivatives and Their Use as Inhibitors and Tools for Comparing the Active Sites of Human Liver Cytochromes P450 of the 2C Subfamily

  摘要：

  Twenty-three new derivatives of sulfaphenazole (SPA) were synthesized to further explore the topology of the active sites of human liver cytochromes P450 of the 2C subfamily and to find new selective inhibitors of these cytochromes. These compounds are derived from SPA by replacement of the NH2 and H (of the SO2NH function) substituents of SPA with various R-1 and R-2 groups, respectively. Their inhibitory effects were studied on recombinant CYP 2C8, 2C9, 2C18, and 2C19 expressed in yeast. High affinities for CYP 2C9 (IC50 < 1 muM) were only observed for SPA derivatives having the SO2NH function and a relatively small R-1 substituent (R-1 = NH2, CH3). Any increase in the size of R-1 led to a moderate decrease of the affinity, and the N-alkylation of the SO2NH function of SPA to a greater decrease of this affinity. The same structural changes led to opposite effects on molecular recognition by CYP 2C8 and 2C18, which generally exhibited similar behaviors. Thus, contrary to CYP 2C9, CYP 2C8 and 2C18 generally prefer neutral compounds with relatively large R-1 and R2 substituents. CYP 2C19 showed an even lower affinity for anionic compounds than CYP 2C8 and 2C18. However, as CYP 2C8 and 2C18, CYP 2C19 showed a much better affinity for neutral compounds derived ftom N-alkylation of SPA and for anionic compounds bearing a larger R, substituent. One of the new compounds (R-1 = methyl, R-2 = propyl) inhibited all human CYP 2Cs with IC50 values between 10 and 20 muM, while another one (R-1 = allyl, R-2 = methyl) inhibited all CYP 2Cs except CYP 2C9, and a third one (R-1 = R-2 = methyl) inhibited all CYP 2Cs except CYP 2C8. Only 2 compounds of the 25 tested derivatives were highly selective toward one human CYP 2C; these are SPA and compound I (Ri = CH3, R2 = H), which acted as selective CYP 2C9 inhibitors. However, some SPA derivatives selectively inhibited CYP 2C8 and 2C18. Since CYP 2C18 is hardly detectable in human liver, these derivatives could be interesting molecules to selectively inhibit CYP 2C8 in human liver microsomes. Thus, compound 11 (R-1 = NH2, R-2 = (CH2)(2)CH(CH3)(2)) appears to be particularly interesting for that purpose as its IC50 value for CYP 2C8 is low (3 muM) and 20-fold smaller than those found for CYP 2C9 and 2C19.

  DOI：

  10.1021/jm010861y

文献信息

• Palladium-catalyzed desulfitative C-arylation of a benzo[d]oxazole C–H bond with arene sulfonyl chlorides
  作者：Manli Zhang、Shouhui Zhang、Miaochang Liu、Jiang Cheng

  DOI：10.1039/c1cc14718h

  日期：——

  A palladium-catalyzed direct desulfitative C-arylation of a benzo[d]oxazole C-H bond with arene sulfonyl chlorides is described. The procedure tolerates halo, cyano, nitro, trifluoromethyl, acetyl and acetylamino groups on the phenyl ring of sulfonyl chlorides, providing the arylation products in moderate to good yields. It represents a practical and attractive alternative for the synthesis of 2-aryl

  描述了苯并[d]恶唑CH键与芳烃磺酰氯的钯催化的直接脱硫C-芳基化。该方法容许磺酰氯苯环上的卤素，氰基，硝基，三氟甲基，乙酰基和乙酰氨基基团，以中等至良好的产率提供芳基化产物。它代表了合成2-芳基苯并恶唑的实用且有吸引力的替代方法。
• Aryl Alkyl Sulfonamides As Therapeutic Agents For The Treatment Of Bone Conditions
  申请人：Ralston Stuart Hamilton

  公开号：US20080119555A1

  公开（公告）日：2008-05-22

  The present invention pertains to certain aryl alkyl sulfonamides and derivatives thereof which, inter alia, inhibit osteoclast survival, formation, and/or activity; and/or inhibit bone resorption, and more particularly to compounds of the formula: wherein: Ar 1 is independently C 5-20 aryl (e.g., biphenyl, phenanthryl, fluorenyl, or carbazolyl, most preferably biphenyl), and is optionally substituted; R N is independently —H, acyl, C 5-20 aryl-C 1-7 alkyl, C 3-20 heterocyclyl, or C 1-7 alkyl, and is optionally substituted; R alk is a C 2-10 alkylene group, and is optionally substituted; and Q is independently —H or an organic group having from 1 to 30 atoms selected from carbon, nitrogen, oxygen, sulfur, phosphorus, fluorine, chlorine, bromine, and iodine (e.g., an oxy-type group, an amine-type group, etc.); and pharmaceutically acceptable salts, solvates, amides, esters, ethers, chemically protected forms, and prodrugs thereof. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit osteoclast survival, formation, and/or activity, and to inhibit conditions mediated by osteoclasts and/or characterised by bone resorption, in the treatment of bone disorders such as osteoporosis, rheumatoid arthritis, cancer associated bone disease, Paget's disease, and the like; and/or in the treatment of conditions associated with inflammation or activation of the immune system.

  本发明涉及某些芳基烷基磺酰胺及其衍生物，其中，它们抑制破骨细胞的存活、形成和/或活性；和/或抑制骨吸收，更具体地说，是式子的化合物： 其中：Ar1独立地是C5-20芳基（例如，联苯、菲、芴或咔唑基，最好是联苯），并且可以选择性地被取代；RN独立地是-H、酰基、C5-20芳基-C1-7烷基、C3-20杂环基或C1-7烷基，并且可以选择性地被取代；Ralk是C2-10烷基链，可以选择性地被取代；Q独立地是-H或具有1-30个由碳、氮、氧、硫、磷、氟、氯、溴和碘选择的有机基团（例如，氧型基团，胺型基团等）；以及其药学上可接受的盐、溶剂化合物、酰胺、酯、醚、化学保护形式和前药。本发明还涉及包含这样的化合物的制药组合物，以及在体外和体内使用这样的化合物和组合物来抑制破骨细胞的存活、形成和/或活性，并抑制由破骨细胞介导和/或通过骨吸收表征的骨疾病的治疗，例如骨质疏松症、类风湿性关节炎、与癌症相关的骨疾病、帕吉特病等；和/或用于治疗与炎症或免疫系统激活有关的疾病。
• [EN] ARYL ALKYL SULFONAMIDES AS THERAPEUTIC AGENTS FOR THE TREATMENT OF BONE CONDITIONS<br/>[FR] ARYLE-ALKYLE SULFONAMIDES UTILISES EN TANT QU'AGENTS THERAPEUTIQUES POUR LE TRAITEMENT DE PATHOLOGIES OSSEUSES
  申请人：UNIV ABERDEEN

  公开号：WO2005118528A3

  公开（公告）日：2006-01-26
• Vizgert, R. V.; Budenkova, N. M.; Maksimenko, N. N., Journal of Organic Chemistry USSR (English Translation), 1985, vol. 21, # 11, p. 2163 - 2165
  作者：Vizgert, R. V.、Budenkova, N. M.、Maksimenko, N. N.

  DOI：——

  日期：——
• ARYL ALKYL SULFONAMIDES AS THERAPEUTIC AGENTS FOR THE TREATMENT OF BONE CONDITIONS
  申请人：The University Court of The University of Aberdeen

  公开号：EP1756046B1

  公开（公告）日：2009-12-09