(+)-4S-3-[1'-oxo-6'-(benzyloxy)hexyl]-4-benzyl-2-oxazolidinone | 143761-23-3

• 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: (+)-4S-3-[1'-oxo-6'-(benzyloxy)hexyl]-4-benzyl-2-oxazolidinone
• 英文别名: (S)-4-benzyl-3-(6-benzyloxy-hexanoyl)-oxazolidin-2-one；4(S)-benzyl-3-[6-(benzyloxy)hexanoyl]oxazolidin-2-one；(4S)-4-benzyl-3-(6-phenylmethoxyhexanoyl)-1,3-oxazolidin-2-one
• CAS: 143761-23-3
• 化学式: C₂₃H₂₇NO₄
• 分子量: 381.472
• InChiKey: WAJYDAZARDQTHZ-NRFANRHFSA-N

物化性质

• 沸点：
  550.0±33.0 °C(Predicted)
• 密度：
  1.168±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+)-4S-3-[1'-oxo-6'-(benzyloxy)hexyl]-4-benzyl-2-oxazolidinone 在 palladium dihydroxide lithium hydroxide 、 正丁基锂 、 氰基磷酸二乙酯 、 1,4-环己二烯 、 水 、 双氧水 、 三乙胺 、 二异丙胺 、 三苯基膦 、 三氟乙酸 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.5h， 生成 (R)-7-(4-Chloro-phenoxy)-3-{(S)-2,2-dimethyl-1-[2-(4-sulfamoyl-phenyl)-ethylcarbamoyl]-propylcarbamoyl}-heptanoic acid
  参考文献：
  名称：

  Inhibition of Matrix Metalloproteinases by Hydroxamates Containing Heteroatom-Based Modifications of the P1' Group

  摘要：

  In this study, structure-based drug design of matrix metalloproteinase inhibitors [human fibroblast collagenase (HFC), human fibroblast stromelysin (HFS), and human neutrophil collagenase (HNC)] was utilized in the development of potent hydroxamates which contain novel, heteroatom-based modifications of the P-1' group. A series containing a P-1' butyramide group resulted in a nanomolar potent and selective HNC inhibitor as well as a dual HFS/HNC inhibitor. Benzylic others with a four- or five-carbon methylene linker in the P-1' position also produced nanomolar potent HFS/HNC inhibition and micromolar potent HFC inhibition as expected. Surprisingly, the phenolic ethers of the same overall length as the benzylic ethers showed nanomolar potencies against HFC, as well as HFS and HNC. The potency profile of the phenolic ethers was optimized by structure-activity relationships of the phenolic group and the C-terminal amide. These inhibitors may help elucidate the in vivo roles of matrix metalloproteinases in normal and disease states.

  DOI：

  10.1021/jm00014a010
• 作为产物：
  描述：

  6-苄氧基己酸 在 草酰氯 、 正己基锂 作用下， 以 甲苯 为溶剂， 生成 (+)-4S-3-[1'-oxo-6'-(benzyloxy)hexyl]-4-benzyl-2-oxazolidinone
  参考文献：
  名称：

  Total Synthesis of 26-Fluoro-epothilone B

  摘要：

  通过尽早引入合成上要求较高的氟甲基环氧化物功能，实现了表霉素 B 衍生物 26-氟表霉素 B (1) 的高效合成。氟取代基的存在显著提高了环氧化物的稳定性，使其能够承受片段偶联步骤和最终转化所需的各种反应条件。

  DOI：

  10.1055/s-2004-817771

文献信息

• Certain (arylsulfonamido- and imidazolyl-)-substituted carboxylic acids
  申请人：Ciba-Geigy Corporation

  公开号：US05153214A1

  公开（公告）日：1992-10-06

  The present invention is concerned with compounds of formula I ##STR1## wherein A, B, M, R, Ar and Het are as defined in the specification, pharmaceutically acceptable ester and amide derivatives thereof; N-oxides thereof, tetrazole derivatives thereof, and salts thereof. These compounds have valuable pharmacological activities, especially as inhibitors of thromboxane synthetase and as receptor antagonists of thromboxane A.sub.2 and prostaglandin H.sub.2.

  本发明涉及以下式I的化合物 ##STR1## 其中A、B、M、R、Ar和Het如规范中所定义，其药学上可接受的酯和酰胺衍生物；其N-氧化物，四唑衍生物和盐。这些化合物具有有价值的药理活性，特别是作为血栓素合酶的抑制剂和血栓素A.sub.2和前列腺素H.sub.2的受体拮抗剂。
• The design, synthesis, and structure-activity relationships of a series of macrocyclic MMP inhibitors
  作者：Douglas H. Steinman、Michael L. Curtin、Robert B. Garland、Steven K. Davidsen、H.Robin Heyman、James H. Holms、Daniel H. Albert、Terry J. Magoc、Ildiko B. Nagy、Patrick A. Marcotte、Junling Li、Douglas W. Morgan、Charles Hutchins、James B. Summers

  DOI：10.1016/s0960-894x(98)00396-5

  日期：1998.8

  A series of succinate-derived hydroxamic acids incorporating a macrocyclic ring were designed, synthesized, and evaluated as inhibitors of matrix metalloproteinases. The inhibitors were designed based on the published X-ray crystal structure of batimastat (1) complexed with human neutrophil collagenase (MMP-8). The synthesized compounds were shown to inhibit selected MMPs in vitro with low nanomolar

  设计，合成并评估了一系列掺入大环的琥珀酸酯衍生的异羟肟酸，并将其评估为基质金属蛋白酶的抑制剂。抑制剂是根据已公布的与人嗜中性粒细胞胶原酶（MMP-8）结合的巴马司他（1）的X射线晶体结构设计的。合成的化合物显示出可在体外以低纳摩尔浓度抑制选定的MMP。
• Certain (arylsulfonamido- and pyridyl- or imidazolyl-)-substituted carboxylic acids and derivatives thereof
  申请人：CIBA-GEIGY AG

  公开号：EP0493324A1

  公开（公告）日：1992-07-01

  The present invention is concerned with compounds of formula I wherein A, B, M, R, Ar and Het are as defined in the specification, pharmaceutically acceptable ester and amide derivatives thereof; N-oxides thereof, tetrazole derivatives thereof, and salts thereof. These compounds have valuable pharmacological activities, especially as inhibitors of thromboxane synthetase and as receptor antagonists of thromboxane A₂ and prostaglandin H₂.

  本发明涉及式 I 的化合物 其中 A、B、M、R、Ar 和 Het 如说明书中所定义；其药学上可接受的酯和酰胺衍生物；其 N-氧化物；其四唑衍生物；以及其盐。这些化合物具有重要的药理活性，特别是作为血栓素合成酶的抑制剂和血栓素 A₂及前列腺素 H₂的受体拮抗剂。
• [EN] A NEW PROCESS FOR THE PREPARATION OF EPOTHILONE DERIVATIVES, NEW EPOTHILONE DERIVATIVES AS WELL AS NEW INTERMEDIATE PRODUCTS FOR THE PROCESS AND THE METHODS OF PREPARING SAME<br/>[FR] NOUVELLE TECHNIQUE DE PREPARATION DE DERIVES D'EPOTHILONE, NOUVEAUX DERIVES DE L'EPOTHILONE ET NOUVEAUX PRODUITS INTERMEDIAIRES UTILISES DANS CETTE TECHNIQUE ET DANS LES PROCEDES DE PREPARATION DE CES DERIVES
  申请人：NOVARTIS AG

  公开号：WO2004024735A3

  公开（公告）日：2004-07-22
• Regio-selective reduction of the C–C double bonds in α,β-unsaturated acyl 4-substituted oxazolidin-2-ones and oxazolidine-2-thiones
  作者：Shao-Gang Li、Jian-Wei Jin、Yikang Wu

  DOI：10.1016/j.tet.2011.11.038

  日期：2012.1

  Selective saturation of the conjugated C-C double bonds in the title compounds was examined in a systematic way for the first time. Many established protocols effective for similar reduction of alpha,beta-unsaturated ketones and esters in the literature were found to be inapplicable in the present context. The most satisfactory results were finally obtained using the DIBAL-H/MeLi/Cul/HMPA/THF conditions. (C) 2011 Elsevier Ltd. All rights reserved.