(4R,5S)-3-(1-氧代-2-溴乙基)-4-甲基-5-苯基-2-恶唑烷酮 | 147595-55-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: (4R,5S)-3-(1-氧代-2-溴乙基)-4-甲基-5-苯基-2-恶唑烷酮
• 英文名称: (4R,5S)-N-bromoacetyl-4-methyl-5-phenyloxazolidin-2-one
• 英文别名: (4R,5S)-3-(1-oxo-2-bromoethyl)-4-methyl-5-phenyl-2-oxazolidinone；3-(1-Bromoacetyl)-4R-methyl-5S-phenyl-2-oxazolidinone；(4R,5S)-3-(2-bromoacetyl)-4-methyl-5-phenyloxazolidin-2-one；(4R,5S)-3-(bromoacetyl)-4-methyl-5-phenyloxazolidin-2-one；(4R,5S)-3-(2-bromoacetyl)-4-methyl-5-phenyl-1,3-oxazolidin-2-one
• CAS: 147595-55-9
• 化学式: C₁₂H₁₂BrNO₃
• 分子量: 298.136
• InChiKey: PQQFQURPXMYVCA-LDYMZIIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R,5S)-3-(1-氧代-2-溴乙基)-4-甲基-5-苯基-2-恶唑烷酮 在 sodium hydride 作用下， 以 四氢呋喃 、 乙二醇二甲醚 为溶剂， 反应 6.0h， 生成 (4R,5S)-(+)-4-甲基-5-苯基-2-恶唑啉酮
  参考文献：
  名称：

  不对称铵基重排：氮不对称的影响

  摘要：

  仅在存在无环烯烃的情况下，相对和绝对立体控制方面，衍生自甘氨酰樟脑的烯丙基铵碘的[2,3]-正向重排具有很高的选择性。当衍生自N-甲基四氢吡啶（'NMTP'）的羟基的手性酯发生重排时，反应显示出独有的顺式-立体选择性，但所获得的产物几乎没有绝对的立体控制。这些观察结果支持N-手性铵基的σ重排受氮立体定向性控制的观点。

  DOI：

  10.1016/j.tet.2006.06.043
• 作为产物：
  描述：

  左旋去甲麻黄碱 在 氢氧化钾 、 sodium hydride 作用下， 反应 1.0h， 生成 (4R,5S)-3-(1-氧代-2-溴乙基)-4-甲基-5-苯基-2-恶唑烷酮
  参考文献：
  名称：

  Radical routes to indolizidines. Synthesis of (-)-slaframine

  摘要：

  The synthesis of (-)-slaframine (5) was executed in 11 steps and 25% overall yield from resolved 3(S)-hydroxy-4-pentenamide (22). Two cyclization reactions were used to form the indolizidine skeleton and also to provide the necessary stereocontrol at C-8a and C-6 of the natural product. "Iodolactamization" of 22 gave selectively the cis-pyrrolidinone 21. Later in the synthesis, a silane-mediated radical cyclization of the phenylseleno lactam 33 gave selectively the 6-alpha-hydroxyindolizidinone 35a, an event predictable from model studies-such as 14c --> 15c. Replacement of hydroxy with azido and reduction of the lactam carbonyl gave "slaframine azide", 38, a stable and easily convertible immediate precursor to 5.

  DOI：

  10.1021/jo00044a011

文献信息

• EPOTHILONE DERIVATIVES, METHOD FOR PRODUCING SAME AND THEIR PHARMACEUTICAL USE
  申请人：——

  公开号：US20030144523A1

  公开（公告）日：2003-07-31

  This invention relates to the new epothilone derivatives of general formula I, 1 in which substituents Y, Z R 2a , R 2b , R 3 , R 4a , R 4b , D—E, R 5 , R 6 , R 7 , R 8 and X have the meanings that are indicated in more detail in the description. The new compounds interact with tubulin by stabilizing microtubuli that are formed. They are able to influence the cell-splitting in a phase-specific manner and are suitable for treating malignant tumors, for example, ovarian, stomach, colon, adeno-, breast, lung, head and neck carcinomas, malignant melanomas, acute lymphocytic and myelocytic leukemia. In addition, they are suitable for anti-angiogenesis therapy as well as for treatment of chronic inflammatory diseases (psoriasis, arthritis). To avoid uncontrolled proliferation of cells and for better compatibility of medical implants, they can be applied or introduced into polymer materials. The compounds according to the invention can be used alone or to achieve additive or synergistic actions in combination with other principles and classes of substances that can be used in tumor therapy.

  本发明涉及具有通式I的新埃波替隆衍生物，其中取代基Y、Z、R2a、R2b、R3、R4a、R4b、D—E、R5、R6、R7、R8和X的含义在描述中更详细地指出。这些新化合物通过与微管蛋白的相互作用来稳定形成的微管。它们能够以阶段特异性的方式影响细胞分裂，并适用于治疗恶性肿瘤，例如卵巢、胃、结肠、腺体、乳腺、肺、头颈癌、恶性黑色素瘤、急性淋巴细胞和骨髓细胞白血病。此外，它们还适用于抗血管生成治疗以及治疗慢性炎性疾病（银屑病、关节炎）。为了避免细胞的不受控制的增殖以及提高医疗植入物的相容性，它们可以应用于或引入到聚合物材料中。根据发明的化合物可以单独使用，也可以与其他可用于肿瘤治疗的原理和物质类别结合使用，以实现相加或协同作用。
• Synthesis of (7<i>S</i>,15<i>S</i>)- and (7<i>R</i>,15<i>S</i>)-Dolatrienoic Acid^1a
  作者：Jonathan J. Duffield、George R. Pettit

  DOI：10.1021/np000502q

  日期：2001.4.1

  stereospecific synthesis of (7S,15S)- and (7R,15S)-dolatrienoic acids (2) was achieved using an approach consisting of 16 linear steps. The C-11--C-16 unit was prepared in seven steps from ethyl (S)-lactate and coupled using a trans-selective Wittig--Schlosser reaction to the C-7--C-10 fragment. Chirality at the C-7 position was introduced using an Evan's-type chiral auxiliary in a cobalt-mediated Reformatsky

  （7S，15S）-和（7R，15S）-十二碳三烯酸（2）的立体有择合成是使用由16个线性步骤组成的方法实现的。C-11--C-16单元是从（S）-乳酸乙酯中分七个步骤制备的，并使用反式Wittig-Schlosser反应与C-7-C-10片段偶联。在钴介导的Reformatsky反应中，使用Evan's型手性助剂在C-7位置引入手性，得到（3S，11S）-醛24。随后与Wittig反应，由三步反应得到的酸形成acid盐， （7S，15S）-十二碳三烯酸，强癌细胞生长抑制性环二肽dolastatin 14（1）的四种非对映异构体之一。第二种非对映异构体（7R，15S）-十二碳三烯酸
• [EN] DERMAL COMPOSITIONS CONTAINING UNNATURAL HYGROSCOPIC AMINO ACIDS<br/>[FR] COMPOSITIONS DERMATOLOGIQUES CONTENANT DES AMINOACIDES HYGROSCOPIQUES NON NATURELS
  申请人：MEDPHARM LTD

  公开号：WO2014072747A1

  公开（公告）日：2014-05-15

  Unnatural, hygroscopic amino acids are useful to enhance the moisture retention and uptake properties of skin. In particular, such amino acids are N-hydroxyserine, N- hydroxyglycine, L-homoserine,alpha-hydroxyglycine, 2-(aminooxy) -2-hydroxyacetic acid, 2-hydroxy-2-(hydroxyamino) acetic acid, 2- (aininooxy)acetic acid, and combinations thereof.

  不自然的、亲水性的氨基酸对增强皮肤的保湿和吸湿性能是有用的。特别是，这些氨基酸包括N-羟基丝氨酸、N-羟基甘氨酸、L-同丝氨酸、α-羟基甘氨酸、2-(氨氧基)-2-羟基乙酸、2-羟基-2-(羟氨基)乙酸、2-(氨氧基)乙酸，以及它们的组合。
• Epothilon derivatives, method for the production and the use thereof as pharmaceuticals
  申请人：Schering, AG

  公开号：US07001916B1

  公开（公告）日：2006-02-21

  Disclosed are epothilone compounds of formula I, which are useful as pharmaceutical compounds for treating, for example, malignant tumors and chronic inflammatory diseases and are useful in anti-angiogenesis therapy.

  揭示了公式I的依托利定化合物，这些化合物可用作治疗恶性肿瘤和慢性炎症性疾病的药物化合物，并在抗血管生成治疗中有用。
• Epothilone derivatives, process for their production, and their pharmaceutical use
  申请人：Klar Ulrich

  公开号：US20060040990A1

  公开（公告）日：2006-02-23

  Disclosed are epothilone compounds of formula I, which are useful as pharmaceutical compounds for treating, for example, malignant tumors and chronic inflammatory diseases and are useful in anti-angiogenesis therapy.

  揭示了公式I的环毛菌素化合物，它们可用作药物化合物，例如治疗恶性肿瘤和慢性炎症性疾病，并在抗血管生成治疗中有用。