D,L-2-isobutyl-3-(methoxycarbonyl)-propanoic acid | 132631-36-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: D,L-2-isobutyl-3-(methoxycarbonyl)-propanoic acid
• 英文别名: 2-(2-methoxy-2-oxoethyl)-4-methylpentanoic acid；D,L-2-isobutyl-3-(methoxycarbonyl)propionic acid；2-iso-butyl-3-(methoxycarbonyl)-propionic acid；2-isobutyl-3-(methoxycarbonyl)-propionic acid
• CAS: 132631-36-8
• 化学式: C₉H₁₆O₄
• 分子量: 188.224
• InChiKey: REUDDXCWANRXHG-UHFFFAOYSA-N

物化性质

• 沸点：
  288.6±23.0 °C(Predicted)
• 密度：
  1.069±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  D,L-2-isobutyl-3-(methoxycarbonyl)-propanoic acid 在 盐酸 、 氢氧化钾 、 盐酸羟胺 、 三乙胺 、 N,N'-羰基二咪唑 作用下， 以 甲醇 、 乙醚 、 氯仿 为溶剂， 反应 26.0h， 生成 伊洛马司他
  参考文献：
  名称：

  Matrix Metalloproteinase Inhibitors:  A Structure−Activity Study

  摘要：

  Modifications around the dipeptide-mimetic core of a hydroxamic acid based matrix metalloproteinase inhibitor were studied. These variations incorporated a variety of natural, unnatural, and synthetic amino acids in addition to modifications of the P1' and P3' substituents. The results of this study indicate the following structural requirements: (1) Two key hydrogen bonds must be present between the enzyme and potent substrates. (2) Potent inhibitors must possess strong zinc-binding functionalities. (3) The potential importance of the hydrophobic group at position R3 as illustrated by its ability to impart greater relative potency against stromelysin when larger hydrophobic groups are used. (4) Requirements surrounding the nature of the amino acid appear to be more restrictive for stromelysin than for neutrophil collagenase, 72 kDa gelatinase, and 92 kDa gelatinase. These requirements may involve planar fused-ring aryl systems and possibly hydrogen-bonding capabilities.

  DOI：

  10.1021/jm970494j
• 作为产物：
  描述：

  (E)-2-(2-methylpropylidene)succinic acid 在 palladium on activated charcoal Amberlyst 15 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、303.98 kPa 条件下， 反应 31.0h， 生成 D,L-2-isobutyl-3-(methoxycarbonyl)-propanoic acid
  参考文献：
  名称：

  将硝基烷烃加成到马来酸二甲酯中。2-烷基琥珀酸的两个单酯的区域选择性形成

  摘要：

  通过将硝基烷烃共轭加成到马来酸二甲酯中而获得的（E）-2-亚烷基琥珀酸的二酯可以在反应性更高的羧基上选择性地单水解成相应的半酯。可选择地，全部水解为二酸允许链烷羧基的随后的选择性甲基酯化，以给出其他区域异构的半酯。可以通过不饱和衍生物的催化加氢最终获得2-烷基琥珀酸单酯。

  DOI：

  10.1016/s0040-4020(03)01175-x

文献信息

• Process for preparing synthetic matrix metalloprotease inhibitors
  申请人：Glycomed Incorporated

  公开号：US05892112A1

  公开（公告）日：1999-04-06

  Synthetic mammalian matrix metalloprotease inhibitors are disclosed that are useful for treating or preventing diseases wherein said diseases are caused by unwanted mammalian matrix metalloprotease activity and include skin disorders, keratoconus, restenosis, rheumatoid arthritis, wounds, cancer, angiogenesis and shock.

  揭示了一种合成的哺乳动物基质金属蛋白酶抑制剂，用于治疗或预防由不需要的哺乳动物基质金属蛋白酶活性引起的疾病，包括皮肤疾病、角膜圆锥症、再狭窄、类风湿关节炎、伤口、癌症、血管生成和休克。
• Novel method of treatment of inflammatory skin conditions
  申请人：Chandler Rupert Stephen

  公开号：US20070049518A1

  公开（公告）日：2007-03-01

  There is provided, inter alia, a method for the treatment or prevention of an inflammatory skin condition which is characterised by colonisation with Staphylococcus aureus , comprising the topical administration of an aureolysin inhibitor.

  提供了一种治疗或预防由金黄色葡萄球菌定植引起的炎症性皮肤病的方法，包括局部施用一种金黄色葡萄球菌溶素抑制剂。
• Inhibitors of TNF-.alpha. secretion
  申请人：Immunex Corporation

  公开号：US05594106A1

  公开（公告）日：1997-01-14

  Compounds and methods are disclosed that are useful in inhibiting the TNF-.alpha. converting enzyme (TACE) responsible for cleavage of TNF-.alpha. precursor to provide biologically active TNF-.alpha.. The compounds employed in the invention are peptidyl derivatives having active groups capable of inhibiting TACE such as, hydroxamates, thiols, phosphoryls and carboxyls.

  本发明揭示了在抑制负责将TNF-.alpha.前体剪切为生物活性TNF-.alpha.的TNF-.alpha.转化酶（TACE）方面有用的化合物和方法。本发明中使用的化合物是具有能够抑制TACE的活性基团的肽类衍生物，如羟肟、硫醇、磷酰基和羧基。
• Inhibition of angiogenesis by synthetic matrix metalloprotease inhibitors
  申请人：——

  公开号：US05268384A1

  公开（公告）日：1993-12-07

  Synthetic mammalian matrix metalloprotease inhibitors are useful in controlling angiogenesis. These compounds are thus useful in controlling the growth of tumors and in controlling neovascular glaucomas.

  合成哺乳动物基质金属蛋白酶抑制剂在控制血管生成方面非常有用。因此，这些化合物对于控制肿瘤的生长和控制新生血管性青光眼非常有用。
• Matrix metalloprotease inhibitors
  申请人：——

  公开号：US05189178A1

  公开（公告）日：1993-02-23

  Compounds of the formulas ##STR1## wherein each R.sup.1 is independently H or alkyl (1-8C) and R.sup.2 is alkyl (1-8C) or wherein the proximal R.sup.1 and R.sup.2 taken together are --(CH.sub.2).sub.p -- wherein p=3-5; R.sup.3 is H or alkyl (1-4C); R.sup.4 is fused or conjugated unsubstituted or substituted bicycloaryl methylene; n is 0, 1 or 2; m is 0 or 1; and X is OR.sup.5 or NHR.sup.5, wherein R.sup.5 is H or substituted or unsubstituted alkyl (1-12C), aryl (6-12C), aryl alkyl (6-16C); or X is an amino acid residue or amide thereof; or X is the residue of a cyclic amine or heterocyclic amine; wherein R.sup.6 is H or lower alkyl (1-4C) and R.sup.7 is H, lower alkyl (1-4C) or an acyl group, and wherein --CONR.sup.3 -- is optionally in modified isosteric form are useful for treating conditions which are characterized by unwanted matrix metalloprotease activities.

  化合物的结构式为##STR1##，其中每个R.sup.1独立地为H或烷基（1-8C），R.sup.2为烷基（1-8C），或者接近的R.sup.1和R.sup.2共同为--(CH.sub.2).sub.p --，其中p=3-5；R.sup.3为H或烷基（1-4C）；R.sup.4为融合或共轭的未取代或取代的双环芳基亚甲基；n为0、1或2；m为0或1；X为OR.sup.5或NHR.sup.5，其中R.sup.5为H或取代或未取代的烷基（1-12C）、芳基（6-12C）、芳基烷基（6-16C）；或X为氨基酸残基或其酰胺；或X为环胺或杂环胺的残基；其中R.sup.6为H或较低烷基（1-4C），R.sup.7为H、较低烷基（1-4C）或酰基，以及--CONR.sup.3 --可以选择以修改的同工异构形式存在，用于治疗其特征为不需要的基质金属蛋白酶活性的病况。