4-amino-3-chloro-N-(5-methyl-isoxazol-3-yl)-benzenesulphonamide

• 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-amino-3-chloro-N-(5-methyl-isoxazol-3-yl)-benzenesulphonamide
• 英文别名: 4-amino-3-chloro-N-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide
• 化学式: C₁₀H₁₀ClN₃O₃S
• mdl: MFCD25676767
• 分子量: 287.727
• InChiKey: NLFVITKESIOKCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  磺胺甲恶唑 在 sodium hypochlorite 、 borate buffer 作用下， 生成 3-氨基-5-甲基异恶唑 、 4-(chloroamino)-N-(5-methylisoxazol-3-yl)benzenesulfonamide 、 4-amino-3-chloro-N-(5-methyl-isoxazol-3-yl)-benzenesulphonamide
  参考文献：
  名称：

  Transformation of the Antibacterial Agent Sulfamethoxazole in Reactions with Chlorine:  Kinetics, Mechanisms, and Pathways

  摘要：

  Sulfamethoxazole (SMX)-a member of the sulfonamide antibacterial class-has been frequently detected in municipal wastewater and surface water bodies in recent years. Kinetics, mechanisms, and products of SMX in reactions with free chlorine (HOCl/OCl-) were studied in detail to evaluate the effect of chlorination processes on the fate of sulfonamides in municipal wastewaters and affected drinking waters. Direct reactions of free available chlorine (FAC) with SMX were quite rapid. A half-life of 23 s was measured under pseudo-first-order conditions ([FAC](0) = 20 AM (1.4 mg/L) and [SMX](0) = 2 muM) at pH 7 and 25 degreesC in buffered reagent water. In contrast, a half-life of 38 h was determined for reactions with combined chlorine (NH2Cl, NHCl2) under similar conditions. Free chlorine reaction rates were first-order in both substrate and oxidant, with specific second-order rate constants of 1.1 x 10(3) and 2.4 x 10(3) M-1 s(-1) for SMX neutral and anionic species, respectively. Investigations with substructure model compounds and identification of reaction products verified that chlorine directly attacks the SMX aniline-nitrogen, resulting in (i) halogenation of the SIVIX aniline moiety to yield a ring-chlorinated product at sub-stoichiometric FAC concentrations (i.e., [FAC](0):[SMX](0) less than or equal to 1) or (ii) rupture of the SMX sulfonamide moiety in the presence of stoichiometric excess of FAC to yield 3-amino-5-methylisoxazole, SO42- (via SO2), and N-chloro-p-benzoquinoneimine. Reaction ii represents an unexpected aromatic amine chlorination mechanism that has not previously been evaluated in great detail. Experiments conducted in wastewater and drinking water matrixes appeared to validate measured reaction kinetics for SMX, indicating that SMX and likely other sulfonamide antibacterials should generally undergo substantial transformation during disinfection of such waters with free chlorine residuals.

  DOI：

  10.1021/es035225z

文献信息

• [EN] PHENYL CARBOXAMIDE AND SULFONAMIDE DERIVATIVES FOR USE AS 11-BETA-HYDROXYSTEROID DEHYDROGENASE<br/>[FR] DERIVES DE CARBOXAMIDE DE PHENYLE ET DE SULFONAMIDE UTILISABLES COMME 11-BETA-HYDROXYSTEROIDE DESHYDROGENASE
  申请人：STERIX LTD

  公开号：WO2005042513A1

  公开（公告）日：2005-05-12

  There is provided a compound having Formula (I) R1-Z-R2 Formula (I) wherein R1 is an optionally substituted phenyl ring; R2 is or comprises an optionally substituted aromatic ring; and Z is -X-Y-L- or -Y-X-L- wherein either X is selected from -S(=O)(=O)- and -C(=O)-, and Y is -NR3-; or X is selected from -S(=O)(=O)- and -S-, and Y is -C(R4)(R5)-; L is an optional linker; and R3, R4 and R5 are each independently selected from H and hydrocarbyl; and wherein when R2 comprises the following structural moiety, Formula (II) wherein Q is an atom selected from the group consisting of S, O, N and C; the compound is selected from compounds of the formulae R1-C(=O)-NR3-L-R2; R1-S(=O)(=O)-C(R4)(R5)-L-R2; R1-S-C(R4)(R5)-L-R2; R1-NR3-S(=O)(=O)-L-R2; R1-NR3-C(=O)-L-R2; R1-C(R4)(R5)-S(=O)(=O)-L-R2; and R1-C(R4)(R5)-S-L-R2. These compounds are useful as 11β-hydroxysteriod dehydrogenase inhibitors in the treatment of i.a. diabetes.

  提供一种具有化学式（I）R1-Z-R2的化合物 其中R1是一个可选择取代的苯环; R2是或包括一个可选择取代的芳香环; Z是-X-Y-L-或-Y-X-L- 其中X被选自-S(=O)(=O)-和-C(=O)-，Y是-NR3-；或X被选自-S(=O)(=O)-和-S-，Y是-C(R4)(R5)-；L是可选的连接物；R3、R4和R5各自独立地选择自H和烃基；当R2包含以下结构基团时，该化合物被选择自以下化合物的化学式 R1-C(=O)-NR3-L-R2；R1-S(=O)(=O)-C(R4)(R5)-L-R2；R1-S-C(R4)(R5)-L-R2；R1-NR3-S(=O)(=O)-L-R2；R1-NR3-C(=O)-L-R2；R1-C(R4)(R5)-S(=O)(=O)-L-R2；和R1-C(R4)(R5)-S-L-R2。这些化合物在治疗糖尿病等疾病中作为11β-羟基类固醇脱氢酶抑制剂非常有用。
• 11beta-hydroxysteroid dehydrogenase inhibitors
  申请人：Vicker Nigel

  公开号：US20050227987A1

  公开（公告）日：2005-10-13

  A compound having Formula I R 1 -Z-R 2 Formula I wherein R 1 is an optionally substituted phenyl ring; R 2 is or comprises an optionally substituted-aromatic ring; and Z is -X-Y-L- or -Y-X-L- wherein either X is selected from —S(═O)(═O)— and —C(═O)—, and Y is —NR 3 —; or X is selected from —S(═O)(═O)— and —S—, and Y is —C(R 4 )(R 5 )—; L is an optional linker; and R 3 , R 4 and R 5 are each independently selected from H and hydrocarbyl; and wherein when R 2 comprises the following structural moiety wherein Q is an atom selected from the group consisting of S, O, N and C; the compound is selected from compounds of the formulae R 1 C(═O)—NR 3 -L-R 2 ; R 1 —S(═O)(═O)—C(R 4 )(R 5 )-L-R 2 ; R 1 —S—C(R 4 )(R 5 )-L-R 2 ; R 1 —NR 3 —S(═O)(═O)-L-R 2 ; R 1 —NR 3 —C(═O)-L-R 2 ; R 1 —C(R 4 )(R 5 )—S(═O)(═O)-L-R 2 ; and R 1 —C(R 4 )(R 5 )—S-L-R 2 .

  化合物的化学式为IR1-Z-R2，其中R1为可选取代的苯环；R2为或包含可选取代的芳香环；Z为-X-Y-L-或-Y-X-L-，其中X选自—S(═O)(═O)—和—C(═O)—，Y为—NR3—；或X选自—S(═O)(═O)—和—S—，Y为—C(R4)(R5)—；L为可选的连接基；R3、R4和R5各自独立选择自H和烃基；当R2包含以下结构基团时Q为S、O、N和C中选择的原子，则该化合物被选择为下列化合物的公式：R1C(═O)—NR3-L-R2；R1—S(═O)(═O)—C(R4)(R5)-L-R2；R1—S—C(R4)(R5)-L-R2；R1—NR3—S(═O)(═O)-L-R2；R1—NR3—C(═O)-L-R2；R1—C(R4)(R5)—S(═O)(═O)-L-R2；和R1—C(R4)(R5)—S-L-R2。
• PHENYL CARBOXAMIDE AND SULFONAMIDE DERIVATIVES FOR USE AS 11-BETA-HYDROXYSTEROID DEHYDROGENASE
  申请人：Sterix Limited

  公开号：EP1675844A1

  公开（公告）日：2006-07-05
• US7230020B2
  申请人：——

  公开号：US7230020B2

  公开（公告）日：2007-06-12
• Transformation of the Antibacterial Agent Sulfamethoxazole in Reactions with Chlorine:  Kinetics, Mechanisms, and Pathways
  作者：Michael C. Dodd、Ching-Hua Huang

  DOI：10.1021/es035225z

  日期：2004.11.1

  Sulfamethoxazole (SMX)-a member of the sulfonamide antibacterial class-has been frequently detected in municipal wastewater and surface water bodies in recent years. Kinetics, mechanisms, and products of SMX in reactions with free chlorine (HOCl/OCl-) were studied in detail to evaluate the effect of chlorination processes on the fate of sulfonamides in municipal wastewaters and affected drinking waters. Direct reactions of free available chlorine (FAC) with SMX were quite rapid. A half-life of 23 s was measured under pseudo-first-order conditions ([FAC](0) = 20 AM (1.4 mg/L) and [SMX](0) = 2 muM) at pH 7 and 25 degreesC in buffered reagent water. In contrast, a half-life of 38 h was determined for reactions with combined chlorine (NH2Cl, NHCl2) under similar conditions. Free chlorine reaction rates were first-order in both substrate and oxidant, with specific second-order rate constants of 1.1 x 10(3) and 2.4 x 10(3) M-1 s(-1) for SMX neutral and anionic species, respectively. Investigations with substructure model compounds and identification of reaction products verified that chlorine directly attacks the SMX aniline-nitrogen, resulting in (i) halogenation of the SIVIX aniline moiety to yield a ring-chlorinated product at sub-stoichiometric FAC concentrations (i.e., [FAC](0):[SMX](0) less than or equal to 1) or (ii) rupture of the SMX sulfonamide moiety in the presence of stoichiometric excess of FAC to yield 3-amino-5-methylisoxazole, SO42- (via SO2), and N-chloro-p-benzoquinoneimine. Reaction ii represents an unexpected aromatic amine chlorination mechanism that has not previously been evaluated in great detail. Experiments conducted in wastewater and drinking water matrixes appeared to validate measured reaction kinetics for SMX, indicating that SMX and likely other sulfonamide antibacterials should generally undergo substantial transformation during disinfection of such waters with free chlorine residuals.