(2S)-ethyl 2-[(2-isopropylsulfanyl-3-oxospiro[3.5]non-1-en-1-yl)amino]-3-{4-[(3,5-dichloroisonicotinoyl)amino]phenyl}propionate | 455263-29-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S)-ethyl 2-[(2-isopropylsulfanyl-3-oxospiro[3.5]non-1-en-1-yl)amino]-3-{4-[(3,5-dichloroisonicotinoyl)amino]phenyl}propionate
• 英文别名: Ethyl (2S)-2-[(2-isopropylsulfanyl-3-oxo-spiro[3.5]non-1-en-1-yl)amino]-3-{4-[(3,5-dichloroisonicotinoyl)amino]phenyl}propanoate；ethyl (2S)-3-[4-[(3,5-dichloropyridine-4-carbonyl)amino]phenyl]-2-[(3-oxo-2-propan-2-ylsulfanylspiro[3.5]non-1-en-1-yl)amino]propanoate
• CAS: 455263-29-3
• 化学式: C₂₉H₃₃Cl₂N₃O₄S
• 分子量: 590.571
• InChiKey: VEYFOLCBBMKOTQ-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  123
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S)-ethyl 2-[(2-isopropylsulfanyl-3-oxospiro[3.5]non-1-en-1-yl)amino]-3-{4-[(3,5-dichloroisonicotinoyl)amino]phenyl}propionate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 (2S)-2-[(2-Isopropylsulfanyl-3-oxo-spiro[3.5]non-1-en-1-yl)amino]-3-{4-[(3,5-dichloroisonicotinoyl)amino]phenyl}propanoic acid
  参考文献：
  名称：

  Efficient Synthesis of 3-Aminocyclobut-2-en-1-ones:  Squaramide Surrogates as Potent VLA-4 Antagonists

  摘要：

  [GRAPHICS]A novel series of uniquely functionalized 3-aminocyclobut-2-en-1-ones has been prepared by facile condensation of a variety of cyclobuta-1,3-diones with a phenylalanine-derived primary amine. These systems subsequently lend themselves to substitution at C-2 by reaction with a variety of electrophilic reagents including N-halosuccinimides, sulfenyl chlorides, and Eschenmoser's salt. Compounds from this novel series are potent antagonists of VLA-4.

  DOI：

  10.1021/ol034701n
• 作为产物：
  描述：

  3-乙氧基螺[3.5]-2-壬烯-1-酮 在 盐酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 48.33h， 生成 (2S)-ethyl 2-[(2-isopropylsulfanyl-3-oxospiro[3.5]non-1-en-1-yl)amino]-3-{4-[(3,5-dichloroisonicotinoyl)amino]phenyl}propionate
  参考文献：
  名称：

  Efficient Synthesis of 3-Aminocyclobut-2-en-1-ones:  Squaramide Surrogates as Potent VLA-4 Antagonists

  摘要：

  [GRAPHICS]A novel series of uniquely functionalized 3-aminocyclobut-2-en-1-ones has been prepared by facile condensation of a variety of cyclobuta-1,3-diones with a phenylalanine-derived primary amine. These systems subsequently lend themselves to substitution at C-2 by reaction with a variety of electrophilic reagents including N-halosuccinimides, sulfenyl chlorides, and Eschenmoser's salt. Compounds from this novel series are potent antagonists of VLA-4.

  DOI：

  10.1021/ol034701n

文献信息

• Phenylalanine enamide derivatives
  申请人：——

  公开号：US20020169336A1

  公开（公告）日：2002-11-14

  Phenylalanine enamide derivatives of formula (1) are described: 1 wherein R 1 is a group Ar 1 L 2 Ar 2 Alk- in which: Ar 1 is an optionally substituted aromatic or heteroaromatic group; L 2 is a covalent bond or a linker atom or group; Ar 2 is an optionally substituted arylene or heteroarylene group; and Alk is a chain —CH 2 —CH(R)13 , —CH═C(R)— or 2 in which R is a carboxylic acid (—CO 2 H) or a derivative or biostere thereof; X is an —O— or —S— atom or —N(R 2 )— group in which: R x , R y and R z which may be the same or different is each a hydrogen atom or an optional substituent; or R z is an atom or group as previously defined and R x and R y are joined together to form an optionally substituted spiro linked cycloaliphatic or heterocycloaliphatic group; and the salts, solvates, hydrates and N-oxides thereof. The compounds are able to inhibit the binding of integrins to their ligands and are of use in the prophylaxis and treatment of immuno or inflammatory disorders or disorders involving the inappropriate growth or migration of cells.

  描述了公式（1）的苯丙氨酸烯酰胺衍生物：其中R1是Ar1L2Ar2Alk-中的一种基团，其中：Ar1是可选择取代的芳香族或杂环芳基；L2是一个共价键或连接原子或基团；Ar2是可选择取代的芳基或杂芳基；Alk是一个链-CH2-CH(R)13，-CH═C(R)-或2其中R是羧酸（-CO2H）或其衍生物或生物立体异构体；X是一个-O-或-S-原子或-N(R2)-基团，其中：Rx、Ry和Rz可能相同也可能不同，分别是氢原子或可选择取代基；或Rz是如前所定义的原子或基团，Rx和Ry结合在一起形成一个可选择取代的螺环联接的环脂肪族或杂环脂肪族基团；以及它们的盐、溶剂合物、水合物和N-氧化物。这些化合物能够抑制整合素与其配体的结合，并可用于预防和治疗免疫或炎症性疾病或涉及细胞不当生长或迁移的疾病。
• Phenylalanine Enamide Derivatives
  申请人：Brand Stephen

  公开号：US20070167483A1

  公开（公告）日：2007-07-19

  Phenylalanine enamide derivatives of formula (1) are described: wherein R 1 is a group Ar 1 L 2 Ar 2 Alk- in which: Ar 1 is an optionally substituted aromatic or heteroaromatic group; L 2 is a covalent bond or a linker atom or group; Ar 2 is an optionally substituted arylene or heteroarylene group; and Alk is a chain in which R is a carboxylic acid (—CO 2 H) or a derivative or biostere thereof; X is an —O— or —S— atom or —N(R 2 )— group in which: R x , R y and R z which may be the same or different is each a hydrogen atom or an optional substituent; or R z is an atom or group as previously defined and R x and R y are joined together to form an optionally substituted spiro linked cycloaliphatic or heterocycloaliphatic group; and the salts, solvates, hydrates and N-oxides thereof. The compounds are able to inhibit the binding of integrins to their ligands and are of use in the prophylaxis and treatment of immuno or inflammatory disorders or disorders involving the inappropriate growth or migration of cells.

  描述了公式（1）的苯丙氨酸烯酰衍生物：其中R1是Ar1L2Ar2Alk-基团，其中：Ar1是可选的取代芳香族或杂芳族基团；L2是共价键或连接原子或基团；Ar2是可选的取代芳烃或杂芳烃基团；Alk是链，在其中R是羧酸（-CO2H）或其衍生物或生物同分异构体；X是一个-O-或-S-原子或-N（R2）-基团，其中：Rx，Ry和Rz可相同或不同，分别是氢原子或可选的取代基团；或Rz是先前定义的原子或基团，而Rx和Ry结合在一起形成可选的取代螺环脂肪族或杂环脂肪族基团；以及其盐，溶剂化合物，水合物和N-氧化物。这些化合物能够抑制整合素与其配体的结合，并用于预防和治疗免疫或炎症性疾病或涉及细胞不适当生长或迁移的疾病。
• PHENYLALANINE ENAMIDE DERIVATIVES POSSESSING A CYCLOBUTENE GROUP, FOR USE AS INTEGRIN INHIBITORS
  申请人：Celltech R & D Limited

  公开号：EP1370531B1

  公开（公告）日：2007-02-28
• US7501437B2
  申请人：——

  公开号：US7501437B2

  公开（公告）日：2009-03-10
• Efficient Synthesis of 3-Aminocyclobut-2-en-1-ones:  Squaramide Surrogates as Potent VLA-4 Antagonists
  作者：Stephen Brand、Benjamin C. de Candole、Julien A. Brown

  DOI：10.1021/ol034701n

  日期：2003.6.1

  [GRAPHICS]A novel series of uniquely functionalized 3-aminocyclobut-2-en-1-ones has been prepared by facile condensation of a variety of cyclobuta-1,3-diones with a phenylalanine-derived primary amine. These systems subsequently lend themselves to substitution at C-2 by reaction with a variety of electrophilic reagents including N-halosuccinimides, sulfenyl chlorides, and Eschenmoser's salt. Compounds from this novel series are potent antagonists of VLA-4.