largazole peptide isostere | 1126530-06-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: largazole peptide isostere
• 英文别名: S-((E)-4-((1²Z,2²Z,2⁴R,5S,8S)-5-isopropyl-2⁴-methyl-3,6,10-trioxo-2⁴,2⁵-dihydro-4,7,11-triaza-1(4,2),2(2,4)-dithiazolacyclododecaphane-8-yl)but-3-en-1-yl) octanethioate；S-[(E)-4-[(5R,8S,11S)-5-methyl-6,9,13-trioxo-8-propan-2-yl-3,17-dithia-7,10,14,19,20-pentazatricyclo[14.2.1.12,5]icosa-1(18),2(20),16(19)-trien-11-yl]but-3-enyl] octanethioate
• CAS: 1126530-06-0
• 化学式: C₂₉H₄₃N₅O₄S₃
• 分子量: 621.89
• InChiKey: FZBLZWMNFPJGGN-SZPBEECKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  41
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  209
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  methyl (S,E)-7-((tert-butyldiphenylsilyl)oxy)-3-(((R)-tert-butylsulfinyl)amino)hept-4-enoate 在 盐酸 、 lithium hydroxide monohydrate 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 水 、 potassium carbonate 、 1-羟基苯并三唑 、 对甲苯磺酸 、 三乙胺 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醚 、 二氯甲烷 、 丙酮 、 乙腈 为溶剂， 反应 81.99h， 生成 largazole peptide isostere
  参考文献：
  名称：

  [EN] SYNTHESIS OF STRUCTURAL ANALOGS OF LARGAZOLE AND ASSOCIATED COMPOUNDS
  [FR] SYNTHÈSE D'ANALOGUES STRUCTURAUX DE LARGAZOLE ET COMPOSÉS ASSOCIÉS

  摘要：

  Disclosed are various synthetic methods to prepare structural analogs of largazole and derivatives thereof. One structural analog is an amide isostere of largazole. Another structural analog replaces the thiazole ring of largazole with a pyridine moiety or an oxazole moiety. Also disclosed are various intermediate compounds obtained when preparing structural analogs of largazole and derivatives thereof, including macrocycle analogs having an alcohol functionality.

  公开号：

  WO2022140144A1

文献信息

• [EN] METHOD FOR PREPARING LARGAZOLE ANALOGS AND USES THEREOF<br/>[FR] PROCÉDÉ DE PRÉPARATION DE PARTICULES CREUSES ET LEURS UTILISATIONS
  申请人：UNIV COLORADO STATE RES FOUND

  公开号：WO2016144665A1

  公开（公告）日：2016-09-15

  Analogs of largazole are described herein. Methods of treating cancer and blood disorders using largazole and largazole analogs and pharmaceutical compositions comprising the same are additionally described herein. Methods for preparing largazole analogs are likewise described.

  本文描述了类似largazole的类似物。此外，还描述了使用largazole和largazole类似物治疗癌症和血液疾病的方法，以及包含它们的药物组合物。同样描述了制备largazole类似物的方法。
• Isoform-selective lysine deacetylase inhibitors
  申请人：WASHINGTON UNIVERSITY

  公开号：US10421778B2

  公开（公告）日：2019-09-24

  Isoform-selective lysine deacetylase inhibitors are described. Inhibitors of the lysine deacetylase enzyme are useful as antitumor drugs and for treating addiction, asthma, cardio-vascular disease, immunosuppression, neurodegenerative diseases, sepsis, sickle-cell disease, uveal melanoma and termination of viral latency, particularly HIV-1 latency.

  介绍了具有同工酶选择性的赖氨酸脱乙酰酶抑制剂。赖氨酸去乙酰化酶抑制剂可用作抗肿瘤药物和治疗成瘾、哮喘、心血管疾病、免疫抑制、神经退行性疾病、败血症、镰状细胞病、葡萄膜黑色素瘤和终止病毒潜伏期，特别是 HIV-1 潜伏期。
• Method for preparing largazole analogs and uses thereof
  申请人：Colorado State University Research Foundation

  公开号：US10676504B2

  公开（公告）日：2020-06-09

  Analogs of largazole are described herein. Methods of treating cancer and blood disorders using largazole and largazole analogs and pharmaceutical compositions comprising the same are additionally described herein. Methods for preparing largazole analogs are likewise described.

  本文描述了拉加唑的类似物。本文还描述了使用拉加唑和拉加唑类似物治疗癌症和血液疾病的方法，以及包含这些类似物的药物组合物。同样也描述了制备拉加唑类似物的方法。
• Bowers, Albert A.; Greshook, Thomas J.; West, Nathan, Journal of the American Chemical Society, 2009, vol. 131, p. 2900 - 2905
  作者：Bowers, Albert A.、Greshook, Thomas J.、West, Nathan、Estiu, Guillermina、Schreiber, Stuart L.、et al.

  DOI：——

  日期：——
• Method for Preparing Largazole Analogs and Uses Thereof
  申请人：Williams Robert M.

  公开号：US20120264794A1

  公开（公告）日：2012-10-18

  Analogs of largazole are described herein. Methods of treating cancer and blood disorders using largazole and largazole analogs and pharmaceutical compositions comprising the same are additionally described herein. Methods for preparing largazole analogs are likewise described.