[3H]-Salinosporamide B | 863126-95-8

• 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: [3H]-Salinosporamide B
• 英文别名: Salinosporamide B；(1R,4R,5S)-1-[(S)-[(1S)-cyclohex-2-en-1-yl]-hydroxymethyl]-4-ethyl-5-methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione
• CAS: 863126-95-8
• 化学式: C₁₅H₂₁NO₄
• 分子量: 279.336
• InChiKey: SCJZQKFFYIGMCI-SHTIJGAHSA-N

物化性质

• 沸点：
  500.4±50.0 °C(Predicted)
• 密度：
  1.262±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [3H]-Salinosporamide B 在 palladium on activated carbon 氢气 作用下， 以 丙酮 为溶剂， 反应 15.0h， 生成 (1R,4R,5S)-1-[(S)-cyclohexyl(hydroxy)methyl]-4-ethyl-5-methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione
  参考文献：
  名称：

  [3.2.0] Heterocyclic compounds and methods of using the same

  摘要：

  本发明涉及具有抗癌，抗炎和抗微生物特性的I-VI式化合物及其衍生物和类似物，以及包括其中一种或多种化合物及其衍生物或类似物的组合物。还公开了包含这些化合物的药物组合物以及使用公开的化合物或药物组合物治疗癌症，炎症和微生物感染的方法。

  公开号：

  US20050288352A1
• 作为产物：
  描述：

  C₂₅H₃₃NO₅Si 在 indium 、 高氯酸 、 四丁基氟化铵 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 氯化铵 、 戴斯-马丁氧化剂 、 溶剂黄146 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 44.5h， 生成 [3H]-Salinosporamide B
  参考文献：
  名称：

  一种简明对映选择性全合成盐孢菌素家族天然产物的策略的演变

  摘要：

  本文描述了通过涉及从简单氨基酸丝氨酸快速构建天然产物的高度修饰的吡咯烷酮核心的策略来全合成盐孢菌胺和肉桂酰胺。这种合成成功的关键是利用丝氨酸衍生的 5-恶唑烷酮作为立体化学控制器的先天特性和前所未有的底物驱动的水解动态动力学分辨率。

  DOI：

  10.1002/anie.202210317

文献信息

• METHODS OF USING [3.2.0] HETEROCYCLIC COMPOUNDS AND ANALOGS THEREOF
  申请人：Palladino Michael

  公开号：US20090182027A1

  公开（公告）日：2009-07-16

  Disclosed are methods of treating cancer, inflammatory conditions, and/or infectious disease in an animal comprising: administering to the animal, a therapeutically effective amount of a heterocyclic compound. The animal is a mammal, preferably a human or a rodent.

  本发明涉及治疗动物癌症、炎症疾病和/或感染性疾病的方法，包括向动物（哺乳动物，优选为人类或啮齿动物）施用有效治疗剂量的杂环化合物。
• Salt formulations for the fermentation of marine microorganisms
  申请人：Triphase Research and Development I Corp.

  公开号：US10011814B2

  公开（公告）日：2018-07-03

  Growth medium are disclosed for use in fermenting a marine microorganism. The medium comprise Potassium, Calcium, Strontium, Borate and Fluoride at specific concentrations. Alternatively, the growth medium comprises cobalt at specified concentrations or comprises vitamin B12 at specified concentrations. Methods of producing certain desired compound by fermentation of a marine microorganism are also disclosed.

  公开了用于海洋微生物发酵的生长培养基。培养基包括特定浓度的钾、钙、锶、硼酸盐和氟化物。另外，生长培养基还包括特定浓度的钴或特定浓度的维生素 B12。还公开了通过海洋微生物发酵生产某些所需化合物的方法。
• WO2007/130404
  申请人：——

  公开号：——

  公开（公告）日：——
• WO2008/124699
  申请人：——

  公开号：——

  公开（公告）日：——
• Salinosporamides D−J from the Marine Actinomycete <i>Salinispora tropica</i>, Bromosalinosporamide, and Thioester Derivatives Are Potent Inhibitors of the 20S Proteasome
  作者：Katherine A. Reed、Rama Rao Manam、Scott S. Mitchell、Jianlin Xu、Sy Teisan、Ta-Hsiang Chao、Gordafaried Deyanat-Yazdi、Saskia T. C. Neuteboom、Kin S. Lam、Barbara C. M. Potts

  DOI：10.1021/np0603471

  日期：2007.2.1

  Salinosporamide A (NPI-0052; 3), a highly potent inhibitor of the 20S proteasome, is currently in phase I clinical trials for the treatment of cancer. During the course of purifying multigram quantities of 3 from Salinispora tropica fermentation extracts, several new salinosporamides were isolated and characterized, most of which represent modifications to the chloroethyl substituent at C-2. Specifically, 3 was isolated along with the known compound salinosporamide B (4), the previously undescribed methyl congener salinosporamide D 7), and C-2 epimers of 3 and 7 (salinosporamides F (9) and G (10), respectively). Salinosporamide I (13), in which the methyl group at the ring junction is replaced with an ethyl group, and the C-5 deshydroxyl analogue salinosporamide J (14), were also identified. Replacement of synthetic sea salt with sodium bromide in the fermentation media produced bromosalinosporamide (12), 4, and its C-2 epimer (11, salinosporamide H). In addition to these eight new salinosporamides, several thioester derivatives were generated semisynthetically. IC50 values for cytotoxicity against human multiple myeloma cell line RPMI 8226 and inhibition of the chymotrypsin-like (CT-L) activity of purified rabbit 20S proteasomes were determined for all compounds. The results indicate that thioesters may directly inhibit the proteasome, albeit with reduced potency compared to their beta-lactone counterparts.