(S)-N-methyl-N-methoxy-2-tert-butoxycarbonylamino-3-(triphenylmethylthio)propionamide | 249507-22-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (S)-N-methyl-N-methoxy-2-tert-butoxycarbonylamino-3-(triphenylmethylthio)propionamide
• 英文别名: N-Boc-S-tritylcystein-N-methoxy-N-methylamide；tert-butyl N-[(2S)-1-[methoxy(methyl)amino]-1-oxo-3-tritylsulfanylpropan-2-yl]carbamate
• CAS: 249507-22-0
• 化学式: C₂₉H₃₄N₂O₄S
• 分子量: 506.666
• InChiKey: PPCGNIONQKAWQY-RUZDIDTESA-N

物化性质

• 密度：
  1.163±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  93.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-N-methyl-N-methoxy-2-tert-butoxycarbonylamino-3-(triphenylmethylthio)propionamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 异丙醇 为溶剂， 生成 tert-butyl (S)-(1-oxo-3-(tritylthio)propan-2-yl)carbamate
  参考文献：
  名称：

  Ulbactin F（一种铁结合天然产物）的生物启发全合成

  摘要：

  来自环境微生物组的天然产物为阐明新药寻找中的生物活性提供了精美的模板。最近发现的一种海洋短芽孢杆菌。代谢物 ulbactin F 被发现可抑制肿瘤细胞迁移和侵袭，IC 50 < 3 μM。在此，我们公开了 ulbactin F 和epi -ulbactin F的首次全合成，这是根据生物合成途径建模的。该支架与人类病原体的铁载体结构相似，但包含源自半胱氨酸的新型三环系统。我们发现ulbactin F形成低亲和力金属配合物，优先选择Fe 3+和Cu 2+，这可能暗示了其环境作用及其抗转移作用机制。

  DOI：

  10.1021/acs.orglett.8b02599
• 作为产物：
  描述：

  二甲羟胺盐酸盐 、 Boc-D-Cys(Trt)-OH 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以86%的产率得到(S)-N-methyl-N-methoxy-2-tert-butoxycarbonylamino-3-(triphenylmethylthio)propionamide
  参考文献：
  名称：

  Ulbactin F（一种铁结合天然产物）的生物启发全合成

  摘要：

  来自环境微生物组的天然产物为阐明新药寻找中的生物活性提供了精美的模板。最近发现的一种海洋短芽孢杆菌。代谢物 ulbactin F 被发现可抑制肿瘤细胞迁移和侵袭，IC 50 < 3 μM。在此，我们公开了 ulbactin F 和epi -ulbactin F的首次全合成，这是根据生物合成途径建模的。该支架与人类病原体的铁载体结构相似，但包含源自半胱氨酸的新型三环系统。我们发现ulbactin F形成低亲和力金属配合物，优先选择Fe 3+和Cu 2+，这可能暗示了其环境作用及其抗转移作用机制。

  DOI：

  10.1021/acs.orglett.8b02599

文献信息

• [EN] MACROCYCLIC THERAPEUTIC AGENTS, METHODS OF MANUFACTURE, AND METHODS OF TREATMENT<br/>[FR] AGENTS THÉRAPEUTIQUES MACROCYCLIQUES, DES MÉTHODES DE FABRICATION, ET MÉTHODES DE TRAITEMENT
  申请人：UNIV FLORIDA

  公开号：WO2015127161A1

  公开（公告）日：2015-08-27

  The instant invention describes macrocyclic compounds having therapeutic activity, and the mechanism and methods of treating disorders such as autoimmune diseases, inflammation, and cancer, tumors and cell proliferation related disorders.

  本发明描述了具有治疗活性的大环化合物，以及治疗自身免疫疾病、炎症、癌症、肿瘤和与细胞增殖有关的疾病的机制和方法。
• JAK KINASE INHIBITOR AND PREPARATION AND APPLICATION THEREOF
  申请人：Minghui Pharmaceutical (Shanghai) Limited

  公开号：EP4119565A1

  公开（公告）日：2023-01-18

  The present invention provides a JAK kinase inhibitor and a preparation and application thereof, and the present invention specifically provides a compound having a structure represented in the following formula I, an enantiomer thereof, or a pharmaceutically acceptable salt thereof. The compound has uniquely advantageous JAK kinase inhibitory activity, and as such may be used for treatment of a disease or illness related to JAK kinase activity or expression level.

  本发明提供一种JAK激酶抑制剂及其制备方法和应用，并且具体地提供一种具有以下结构式I的化合物、其对映体，或者其药学上可接受的盐。该化合物具有独特优势的JAK激酶抑制活性，因此可用于治疗与JAK激酶活性或表达水平相关的疾病或病症。
• Improved Total Synthesis and Biological Evaluation of Potent Apratoxin S4 Based Anticancer Agents with Differential Stability and Further Enhanced Activity
  作者：Qi-Yin Chen、Yanxia Liu、Weijing Cai、Hendrik Luesch

  DOI：10.1021/jm4019965

  日期：2014.4.10

  Apratoxins are cytotoxic natural products originally isolated from marine cyanobacteria that act by preventing cotranslational translocation early in the secretory pathway to downregulate receptor levels and inhibit growth factor secretion, leading to potent antiproliferative activity. Through rational design and total synthesis of an apratoxin A/ E hybrid, apratoxin S4 (1a), we have previously improved the antitumor activity and tolerability in vivo. Compound la and newly designed analogues apratoxins S7-S9 (1b-d), with various degrees of methylation at C34 (1b,c) or epimeric configuration at C30 (1d), were efficiently synthesized utilizing improved procedures. Optimizations have been applied to the synthesis of key intermediate aldehyde 7 and further include the application of Leighton's silanes and modifications of Kelly's methods to induce thiazoline ring formation in other crucial steps of the apratoxin synthesis. Apratoxin S9 (1d) exhibited increased activity with subnanomolar potency. Apratoxin S8 (lc) lacks the propensity to be deactivated by dehydration and showed efficacy in a human HCT116 xenograft mouse model.
• Total Synthesis of Apratoxin A
  作者：Takayuki Doi、Yoshitaka Numajiri、Asami Munakata、Takashi Takahashi

  DOI：10.1021/ol052907d

  日期：2006.2.1

  [GRAPHICS]We have achieved a total synthesis of apratoxin A in which thiazoline formation was accomplished from the moCys containing amide 4 using PPh3(0)/Tf2O. Deprotection of the Troc and allyl ester in 17, coupling with tripeptide 3, and deprotection of the allyl ester and the Fmoc, followed by macrolactamization provided apratoxin A (1).
• MACROCYCLIC THERAPEUTIC AGENTS, METHODS OF MANUFACTURE, AND METHODS OF TREATMENT
  申请人：University of Florida Research Foundation

  公开号：EP3107919A1

  公开（公告）日：2016-12-28