4(R)-benzyl-3-(2(R)-chlorosulfonylmethyl-3-methylbutyryl)oxazolidin-2-one | 424822-01-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 4(R)-benzyl-3-(2(R)-chlorosulfonylmethyl-3-methylbutyryl)oxazolidin-2-one
• 英文别名: 4-(R)-benzyl-3-(2-(R)-chlorosulfonylmethyl-3 methylbutyryl)oxazolidin-2-one；(2R)-2-[(4R)-4-benzyl-2-oxo-1,3-oxazolidine-3-carbonyl]-3-methylbutane-1-sulfonyl chloride
• CAS: 424822-01-5
• 化学式: C₁₆H₂₀ClNO₅S
• 分子量: 373.857
• InChiKey: HABVMTVKFOZXRX-ZIAGYGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  89.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4(R)-benzyl-3-(2(R)-chlorosulfonylmethyl-3-methylbutyryl)oxazolidin-2-one 在 lithium hydroxide 、 草酰氯 、 双氧水 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 生成 (2R)-2-[[2-(4-chlorophenoxy)ethyl-methylsulfamoyl]methyl]-N-hydroxy-3-methylbutanamide
  参考文献：
  名称：

  An enantioselective synthesis of sulphonamide hydroxamic acids as matrix metalloproteinase inhibitors

  摘要：

  A high yielding and enantioselective synthesis of alpha-substituted hydroxamic acids as inhibitors of matrix metalloproteinases is described. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(01)02151-7
• 作为产物：
  描述：

  4(R)-benzyl-3-(2(R)-acetylthiomethyl-3-methylbutyryl)oxazolidin-2-one 在 水 、 氯 作用下， 以 二氯甲烷 为溶剂， 生成 4(R)-benzyl-3-(2(R)-chlorosulfonylmethyl-3-methylbutyryl)oxazolidin-2-one
  参考文献：
  名称：

  [EN] HYDROXAMATE SULFONAMIDES AS CD23 SHEDDING INHIBITORS
  [FR] HYDROXAMATE SULFONAMIDES UTILISES EN TANT QU'INHIBITEURS DE L'ELIMINATION DE CD23

  摘要：

  一类哌啶和相关杂环衍生物，C位被取代的芳基或杂芳基基团取代，N位被乙磺酰基团取代，该基团在2位上被羟肟酸基团以及一系列替代取代基取代，作为CD23脱落的强效抑制剂，在治疗和/或预防过敏、炎症和肿瘤疾病方面是有用的。

  公开号：

  WO2004113298A1

文献信息

• [EN] HYDROXAMATE SULFONAMIDES AS CD23 SHEDDING INHIBITORS<br/>[FR] SULFONAMIDES D'HYDROXAMATE SERVANT D'INHIBITEURS D'ELIMINATION DU VIRUS CD23
  申请人：CELLTECH R&D LTD

  公开号：WO2004113312A1

  公开（公告）日：2004-12-29

  A class of piperazine and related heterocyclic derivatives, substituted at the 4-position by a substituted aryl or heteroaryl moiety, and at the 1-position by an ethylsulfonyl group which in turn is substituted at the 2-position by a hydroxamic acid moiety and also by a range of alternative substituents, being potent inhibitors of CD23 shedding, are useful in the treatment and/or prevention of allergic, inflammatory and neoplastic diseases.

  一类哌嗪和相关杂环衍生物，其在4位被取代芳基或杂环基取代，并在1位被乙磺酰基取代，乙磺酰基在2位被羟肟酸基取代，同时还被一系列替代基取代，这些化合物是CD23脱落的有效抑制剂，可用于治疗和/或预防过敏、炎症和肿瘤性疾病。
• [EN] HYDROXAMATE SULFONAMIDES AS CD23 SHEDDING INHIBITORS<br/>[FR] HYDROXAMATE SULFONAMIDES UTILISES EN TANT QU'INHIBITEURS DE L'ELIMINATION DE CD23
  申请人：CELLTECH R&D LTD

  公开号：WO2004113298A1

  公开（公告）日：2004-12-29

  A class of piperidine and related heterocyclic derivatives, C-substituted by a substituted aryl or heteroaryl moiety, and N-substituted by an ethylsulfonyl group which in turn is substituted at the 2-position by a hydroxamic acid moiety and also by a range of alternative substituents, being potent inhibitors of CD23 shedding, are useful in the treatment and/or prevention of allergic, inflammatory and neoplastic diseases.

  一类哌啶和相关杂环衍生物，C位被取代的芳基或杂芳基基团取代，N位被乙磺酰基团取代，该基团在2位上被羟肟酸基团以及一系列替代取代基取代，作为CD23脱落的强效抑制剂，在治疗和/或预防过敏、炎症和肿瘤疾病方面是有用的。
• Hydroxamic and carboxylic acid derivatives
  申请人：——

  公开号：US20020013333A1

  公开（公告）日：2002-01-31

  A pharmacologically active compound of formula (I) 1 wherein R 1 is OH or NHOH; R 2 is H, alklyl, alkenyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, cycloalkyl, cycloalkylalkyl, heterocyclo or heterocycloalkyl (any of which may be optionally substituted with one or more substituents selected from R 6 , W and WR 6 ); and R 3 is H or alkyl; or R 2 , R 3 and the carbon atom to which they are attached together represent a carbocyclic or heterocyclic ring (either of which may be substituted with one or more substituents selected from R 6 , W and WR 6 ), R 4 is alkyl, cycloalkyl, OR 9 , CO 2 R 14 , COR 10 , S(O) q R 10 where q is 0, 1 or 2, CONR 7 R 8 , CN or S(O) q NR 7 R 8 , two R 4 substituents may be attached to the same carbon atom to form C(R 4 ) 2 , where each R 4 is the same or different, or C(R 4 ) 2 may represent C═O; R 5 is alkyl, cycloalkyl, aryl, heteroaryl, heterocyclo, CF 3 , OR 9 , COR 10 , S(O) q R 10 , CO 2 R 14 , CONR 7 R 8 , S(O) q NR 7 R 8 , halogen, NR 10 R 11 or CN, or two adjacent R 5 substituents may be combined to form a heterocyclic ring, R 6 is OR 9 , COR 10 , CO 2 R 15 , CONR 7 R 8 , NR 10 R 11 , S(O) q R 10 , S(O) q NR 7 R 5 , ═O, ═NOR 10 , succinimido or the group 2 R 7 and R 8 , which may be the same or different, are each H, alkyl, cycloalkyl, aryl, heteroaryl, heterocyclo, arylalkyl, heteroarylakyl, heterocycloalkyl or cycloalkylalkyl, or R 7 and R 8 and the nitrogen to which they are attached together represent a heterocyclic ring, R 9 is H, alkyl, CF 3 , CHF 2 , CH 2 F, cycloalkyl, aryl, heteroaryl, heterocyclo, arylalkyl, heteroarylalkyl, heterocycloalkyl or cycloalkylalkyl; R 10 is H, alkyl, cycloalklyl, aryl, heteroaryl, heterocyclo, arylalkyl, heteroarylalkyl, heterocycloalkyl or cycloalkylalkyl; and R 11 is H, alkyl, cycloalkyl, aryl, heteroaryl, heterocyclo, arylalkyl, heteroarylalkyl, heterocycloalkyl, cycloalkylalkyl, COR 12 , CONR 7 R 8 , S(O) q R 12 or S(O) q NR 7 R 8 ; or R 10 and R 11 and the nitrogen to which they are attached together represent a heterocyclic ring, R 12 is OR 9 or R 13 ; R 13 is alkyl, cycloalkyl, aryl, heteroaryl, heterocyclo, arylalkyl, heterarylalkyl, heterocycloalkyl or cycloalkylalkyl; R 14 is H, alkyl or cycloalkyl; R 15 is Y, alkyl, cycloalkyl, arylalkyl or heteroarylalkyl; X is a bond (i.e. is absent), —O— 2 —C(O)—, —S(O) q —, —N(R 11 )—, —N(R 11 )C(R 16 ) 2 —, —S(O) q C(R 16 ) 2 —, —C(R 16 ) 2 N(R 11 )—, —C(R 16 ) 2 S(O) q —, —C(R 16 )═N—, —N═C(R 16 )—, —N(R 11 )SO 2 —, —SO 2 N(R 11 )—, —N(R 11 )CO— or —CON(R 11 )—; and the R 16 groups in C(R 16 ) 2 may be the same or different, Y is a bond (i.e. is absent), —O—, —C(O)—, —S(O) q —, —N(R 11 )—, —N(R 11 )C(R 16 ) 2 —, —S(O) q C(R 16 ) 2 —, —C(R 16 ) 2 N(R 11 )—, —C(R 16 ) 2 S(O) q —, —C(R 16 )—N—, —N═C(R 16 )—, —N(R 11 )SO 2 —, —SO 2 N(R 11 )—, —N(R 11 )CO— or —CON(R 11 )—; and the R 16 groups in C(R 16 ) 2 may be the same or different, R 16 is H, alkyl, cycloalkyl, OR 9 , CO 2 R 14 , COR 10 , S(O) q R 10 , CONR 7 R 8 , CN or S(O) q NR 7 R 8 ; R 17 is H or alkyl; W is alkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocyclo or heterocycloalkyl, represents a single or double bond, each k and m is independently 0, 1, 2 or 3, n is 0, 1 or 2; and p is 0, 1 or 2, provided that n+p does not exceed 3, or a salt, solvate, hydrate, N-oxide, protected amino, protected carboxy or protected hydroxamic acid derivative thereof

  一种化学式（I）的药理活性化合物，其中R1为OH或NHOH；R2为H，烷基，烯基，芳基，芳基烷基，杂芳基，杂芳基烷基，环烷基，环烷基烷基，杂环烷基或杂环烷基烷基（其中任何一个可以选择性地用R6，W和WR6中的一个或多个取代基取代）；R3为H或烷基；或者R2，R3和它们所连接的碳原子共同表示一个碳环或杂环（其中任何一个可以选择性地用R6，W和WR6中的一个或多个取代基取代），R4为烷基，环烷基，OR9，CO2R14，COR10，S（O）qR10（其中q为0，1或2），CONR7R8，CN或S（O）qNR7R8，两个R4取代基可以连接到同一个碳原子上形成C（R4）2，其中每个R4相同或不同，或C（R4）2可以表示C═O；R5为烷基，环烷基，芳基，杂芳基，杂环烷基，CF3，OR9，COR10，S（O）qR10，CO2R14，CONR7R8，S（O）qNR7R8，卤素，NR10R11或CN，或者相邻的两个R5取代基可以结合形成杂环；R6为OR9，COR10，CO2R15，CONR7R8，NR10R11，S（O）qR10，S（O）qNR7R5，═O，═NOR10，琥珀酰亚胺或2R7和R8的基团，它们可以相同或不同，分别为H，烷基，环烷基，芳基，杂芳基，杂环烷基，芳基烷基，杂芳基烷基，杂环烷基烷基或环烷基烷基，或者R7和R8及它们所连接的氮共同表示一个杂环；R9为H，烷基，CF3，CHF2，CH2F，环烷基，芳基，杂芳基，杂环烷基，芳基烷基，杂芳基烷基，杂环烷基烷基或环烷基烷基；R10为H，烷基，环烷基，芳基，杂芳基，杂环烷基，芳基烷基，杂芳基烷基，杂环烷基烷基或环烷基烷基；R11为H，烷基，环烷基，芳基，杂芳基，杂环烷基，芳基烷基，杂芳基烷基，杂环烷基烷基，环烷基烷基，COR12，CONR7R8，S（O）qR12或S（O）qNR7R8；或者R10和R11及它们所连接的氮共同表示一个杂环；R12为OR9或R13；R13为烷基，环烷基，芳基，杂芳基，杂环烷基，芳基烷基，杂芳基烷基或杂环烷基烷基；R14为H，烷基或环烷基；R15为Y，烷基，环烷基，芳基烷基或杂芳基烷基；X为键（即不存在），—O—2—C（O）—，—S（O）q—，—N（R11）—，—N（R11）C（R16）2—，—S（O）qC（R16）2—，—C（R16）2N（R11）—，—C（R16）2S（O）q—，—C（R16）═N—，—N═C（R16）—，—N（R11）SO2—，—SO2N（R11）—，—N（R11）CO—或—CON（R11）—；C（R16）2中的R16取代基可以相同或不同；Y为键（即不存在），—O—，—C（O）—，—S（O）q—，—N（R11）—，—N（R11）C（R16）2—，—S（O）qC（R16）2—，—C（R16）2N（R11）—，—C（R16）2S（O）q—，—C（R16）—N—，—N═C（R16）—，—N（R11）SO2—，—SO2N（R11）—，—N（R11）CO—或—CON（R11）—；C（R16）2中的R16取代基可以相同或不同；R16为H，烷基，环烷基，OR9，CO2R14，COR10，S（O）qR10，CONR7R8，CN或S（O）qNR7R8；R17为H或烷基；W为烷基，环烷基，环烷基烷基，芳基，芳基烷基，杂芳基，杂芳基烷基，杂环烷基或杂环烷基烷基，表示单键或双键，每个k和m独立地为0，1，2或3，n为0，1或2；p为0，1或2，但n+p不得超过3；或其盐，溶剂化合物，水合物，N-氧化物，保护氨基，保护羧基或保护羟胺酸衍生物。
• Hydroxamic acid derivatives
  申请人：——

  公开号：US20030216404A1

  公开（公告）日：2003-11-20

  The invention encompasses novel compounds which are inhibitors of matrix metalloproteinase, ADAM or ADAM-TS enzymes, and which are useful for the treatment of diseases mediated by those enzymes, including degenerative diseases and certain cancers.

  本发明涵盖了一些新型的化合物，这些化合物是基质金属蛋白酶、ADAM或ADAM-TS酶的抑制剂，并且对于治疗由这些酶介导的疾病，包括退行性疾病和某些癌症，具有有益的作用。
• Hydroxamate sulfonamides as cd23 shedding inhibitors
  申请人：Owen Alan David

  公开号：US20060241118A1

  公开（公告）日：2006-10-26

  A class of piperazine and related heterocyclic derivatives, substituted at the 4-position by a substituted aryl or heteroaryl moiety, and at the 1-position by an ethylsulfonyl group which in turn is substituted at the 2-position by a hydroxamic acid moiety and also by a range of alternative substituents, being potent inhibitors of CD23 shedding, are useful in the treatment and/or prevention of allergic, inflammatory and neoplastic diseases.

  一类哌嗪和相关杂环衍生物，其在4-位被取代芳基或杂芳基取代，1-位被乙烷基磺酰基取代，该基团在2-位被羟肟酸基团和多种替代基团取代，是CD23脱落的有效抑制剂，可用于过敏、炎症和肿瘤疾病的治疗和/或预防。