4-[(甲基磺酰基)氨基]苯磺酰胺 | 4426-90-8

• 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: 4-[(甲基磺酰基)氨基]苯磺酰胺
• 英文名称: 4-(methanesulfonamido)benzenesulfonamide
• 英文别名: 4-(N-Methylsulfonamido)-1-sulfonamidobenzol；N-methanesulfonyl-sulfanilic acid amide；N-Methansulfonyl-sulfanilsaeure-amid；4-Methanesulfonylamino-benzenesulfonamide
• CAS: 4426-90-8
• 化学式: C₇H₁₀N₂O₄S₂
• mdl: MFCD00583283
• 分子量: 250.299
• InChiKey: KPLRLDFXFOARQY-UHFFFAOYSA-N

物化性质

• 熔点：
  180-181 °C(Solv: water (7732-18-5))
• 沸点：
  461.4±55.0 °C(Predicted)
• 密度：
  1.575±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  123
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-[(甲基磺酰基)氨基]苯磺酰胺 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 N'-[2-[[2-(diaminomethylideneamino)-1,3-thiazol-4-yl]methylsulfanyl]ethyl]-N-[4-(methanesulfonamido)phenyl]sulfonylmethanimidamide;hydrochloride
  参考文献：
  名称：

  Inhibitors of gastric acid secretion: N-sulphonyl formamidines in a series of new histamine H2-receptor antagonists

  摘要：

  DOI：

  10.1016/0223-5234(88)90174-2
• 作为产物：
  描述：

  甲基磺酰氯 、 磺胺 在 吡啶 作用下， 以 乙腈 为溶剂， 生成 4-[(甲基磺酰基)氨基]苯磺酰胺
  参考文献：
  名称：

  Carbonic anhydrase inhibitors. Part 61. Quantum chemical QSAR of a group of benzenedisulfonamides

  摘要：

  The synthesis of a large group of benzenesulfonamides containing both a primary and secondary sulfonamide moiety is described. These compounds are powerful inhibitors of several isozymes of the enzyme carbonic anhydrase. Separate QSAR's are given for inhibition of three of these isozymes, using descriptors mainly derived from molecular orbital calculations by the semiempirical AM1 method. Activity was found to depend on electrostatic potential-based charges on the atoms of both sulfonamide groups, HOMO and LUMO energies, dipole moments, and lipophilicities. These results are compared with those from other studies. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80096-8

文献信息

• II. Novel HCV NS5B polymerase inhibitors: Discovery of indole C2 acyl sulfonamides
  作者：Gopinadhan N. Anilkumar、Oleg Selyutin、Stuart B. Rosenblum、Qingbei Zeng、Yueheng Jiang、Tin-Yau Chan、Haiyan Pu、Li Wang、Frank Bennett、Kevin X. Chen、Charles A. Lesburg、Jose Duca、Stephen Gavalas、Yuhua Huang、Patrick Pinto、Mousumi Sannigrahi、Francisco Velazquez、Srikanth Venkatraman、Bancha Vibulbhan、Sony Agrawal、Eric Ferrari、Chuan-kui Jiang、H.-C. Huang、Neng-Yang Shih、F. George Njoroge、Joseph A. Kozlowski

  DOI：10.1016/j.bmcl.2011.10.041

  日期：2012.1

  Development of SAR at the C2 position of indole lead 1, a palm site inhibitor of HCV NS5B polymerase (NS5B IC50 = 0.053 μM, replicon EC50 = 4.8 μM), is described. Initial screening identified an acyl sulfonamide moiety as an isostere for the C2 carboxylic acid group. Further SAR investigation resulted in identification of acyl sufonamide analog 7q (NS5B IC50 = 0.039 μM, replicon EC50 = 0.011 μM) with

  描述了在吲哚先导1的 C2 位置发生 SAR，这是一种手掌部位的 HCV NS5B 聚合酶抑制剂（NS5B IC 50  = 0.053 μM，复制子 EC 50  = 4.8 μM）。初步筛选确定了一个酰基磺酰胺部分作为 C2 羧酸基团的等排体。进一步的 SAR 研究发现，酰基磺酰胺类似物7q (NS5B IC 50  = 0.039 μM，复制子 EC 50  = 0.011 μM) 的复制子活性提高了 100 倍以上。
• Footprint Catalysis. II. Molecular Recognition of Footprint Catalytic Sites
  作者：Kensaku Morihara、Emiko Nishihata、Mari Kojima、Sayoko Miyake

  DOI：10.1246/bcsj.61.3999

  日期：1988.11

  In order to investigate the molecular recognition capability of “footprint” catalytic sites, the affinities of nine “footprint” catalysts for eleven competitive inhibitors, closely related to template molecules, were estimated through the competitive inhibition constants, Ki. An examination of the affinity revealed that the recognition by “footprint” catalytic sites was so highly specific that it could recognize not only the whole, but also the partial, structures of the bound molecules.

  为了研究 "足印 "催化位点的分子识别能力，我们通过竞争抑制常数 Ki 估算了九种 "足印 "催化剂对十一种与模板分子密切相关的竞争性抑制剂的亲和力。对亲和力的研究表明，"足印 "催化位点的识别具有高度特异性，不仅能识别结合分子的整体结构，还能识别其部分结构。
• Reagent for determination of hydrogen peroxide
  申请人：Okabe Kazuaki

  公开号：US20050130251A1

  公开（公告）日：2005-06-16

  A reagent for determination of hydrogen peroxide which comprises (A) a compound represented by the following general formula (I): R 1 —NH—R 2 (I) (wherein R 1 represents a carbamoyl group or the like, and R 2 represents an arylamino group, a heteroarylamino group, or a substituent represented by the following general formula (II): [wherein R 3 to R 6 represent X—Y—R a R a represents a hydrogen atom, an alkyl group or the like, X represents a single bond, O or the like, and Y represents a single bond, (C═O) or the like}, a cyano group, a halogen atom or the like]>; (B) a compound represented by the general formula (III): [wherein R 9 represents a group which can be eliminated by oxidative coupling color-developing reaction with the compound represented by the formula (I), and R 7 , R 8 , and R 10 to R 13 have the same meaning as that of R 3 ], or the like; and (C) a peroxidative substance.

  一种用于测定双氧水的试剂，包括（A）由下列通式（I）表示的化合物：R1—NH—R2（I）（其中，R1表示氨甲酰基或类似物，R2表示芳基氨基基团、杂芳基氨基基团或下列通式（II）表示的取代基：[其中R3至R6表示X—Y—RaRa表示氢原子、烷基或类似物，X表示单键、O或类似物，Y表示单键、（C═O）或类似物}、氰基、卤素原子或类似物]>；（B）由通式（III）表示的化合物：[其中R9表示可以通过氧化偶合显色反应与通式（I）表示的化合物发生消除的基团，R7、R8和R10至R13具有与R3相同的含义]或类似物；以及（C）过氧化物质。
• REAGENT FOR DETERMINING HYDROGEN PEROXIDE
  申请人：KYOWA MEDEX CO., LTD.

  公开号：EP1424554A1

  公开（公告）日：2004-06-02

  A reagent for determination of hydrogen peroxide which comprises (A) a compound represented by the following general formula (I):         R1-NH-R2   (I) (wherein R1 represents a carbamoyl group or the like, and R2 represents an arylamino group, a heteroarylamino group, or a substituent represented by the following general formula (II): [wherein R3 to R6 represent X-Y-Ra Ra represents a hydrogen atom, an alkyl group or the like, X represents a single bond, O or the like, and Y represents a single bond, (C=O) or the like}, a cyano group, a halogen atom or the like]> ; (B) a compound represented by the general formula (III): [wherein R9 represents a group which can be eliminated by oxidative coupling color-developing reaction with the compound represented by the formula (I), and R7, R8, and R10 to R13 have the same meaning as that of R3], or the like; and (C) a peroxidative substance.

  一种测定过氧化氢的试剂，它包括(A) 下述通式(I)所代表的化合物： R1-NH-R2 (I) (其中 R1 代表氨基甲酰基或类似基团，R2 代表芳基氨基基团、杂芳基氨基基团或下 列通式(II)所代表的取代基： [其中 R3 至 R6 代表 X-Y-Ra Ra 代表氢原子、烷基或类似物，X 代表单键、O 或类似物，Y 代表单键、（C=O）或类似物}、氰基、卤素原子或类似物]>； (B) 由通式（III）代表的化合物： [其中 R9 代表可通过与式 (I) 所代表的化合物进行氧化偶联显色反应而消除的基团，R7、R8 和 R10 至 R13 的含义与 R3 相同]，或类似物质；以及 (C) 过氧化物。
• Hepatoselectivity of statins: Design and synthesis of 4-sulfamoyl pyrroles as HMG-CoA reductase inhibitors
  作者：William K.C. Park、Robert M. Kennedy、Scott D. Larsen、Steve Miller、Bruce D. Roth、Yuntao Song、Bruce A. Steinbaugh、Kevin Sun、Bradley D. Tait、Mark C. Kowala、Bharat K. Trivedi、Bruce Auerbach、Valerie Askew、Lisa Dillon、Jeffrey C. Hanselman、Zhiwu Lin、Gina H. Lu、Andrew Robertson、Catherine Sekerke

  DOI：10.1016/j.bmcl.2007.11.124

  日期：2008.2

  4-Sulfamoyl pyrroles were designed as novel hepatoselective HMG-CoA reductase inhibitors (statins) to reduce myalgia, a statin-induced adverse effect. The compounds were prepared via a [3 + 2] cycloaddition of a Munchnone with a sulfonamide-substituted alkyne. We identified compounds with greater selectivity for hepatocytes compared to L6-myocytes than rosuvastatin and atorvastatin. There was an inverse correlation of myocyte potencies and ClogP values. A number of analogs were effective at reducing cholesterol in acute and chronic in vivo models but they lacked sufficient chronic in vivo activity to warrant further development. (C) 2007 Elsevier Ltd. All rights reserved.