N-[2-(benzo[b]thiophen-3-yl)ethyl]-S-methyldithiocarbamate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: N-[2-(benzo[b]thiophen-3-yl)ethyl]-S-methyldithiocarbamate
• 英文别名: Brassinin derivative, 3；methyl N-[2-(1-benzothiophen-3-yl)ethyl]carbamodithioate
• 化学式: C₁₂H₁₃NS₃
• 分子量: 267.44
• InChiKey: GCJGCNAYEGRSAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  97.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  二硫化碳 、 2-(苯并[b]噻吩-3-基)乙胺 、 碘甲烷 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以22%的产率得到N-[2-(benzo[b]thiophen-3-yl)ethyl]-S-methyldithiocarbamate
  参考文献：
  名称：

  Structure−Activity Study of Brassinin Derivatives as Indoleamine 2,3-Dioxygenase Inhibitors

  摘要：

  A screen of indole-based structures revealed the natural product brassinin to be a moderate inhibitor of indoleamine 2,3-dioxygenase (IDO), a new cancer immunosuppression target. A structure-activity study was undertaken to determine which elements of the brassinin structure could be modified to enhance potency. Three important discoveries have been made, which will impact future IDO inhibitor development: (i) The dithiocarbamate portion of the brassinin lead is a crucial moiety, which may be binding to the heme iron of IDO; (ii) an indole ring is not necessary for IDO inhibition; and (iii) substitution of the S-methyl group of brassinin with large aromatic groups provides inhibitors that are three times more potent in vitro than the most commonly used IDO inhibitor, 1-methyl-tryptophan.

  DOI：

  10.1021/jm0508888

文献信息

• Novel IDO inhibitors and methods of use thereof
  申请人：Prendergast C. George

  公开号：US20070105907A1

  公开（公告）日：2007-05-10

  Novel indoleamine 2,3-dioxygenase (IDO) inhibitors, compositions comprising the same, and methods of use thereof are disclosed.

  披露了新型的吲哚胺2,3-双加氧酶（IDO）抑制剂，包含该抑制剂的组合物以及使用它们的方法。
• NANO-ENABLED IMMUNOTHERAPY IN CANCER
  申请人：The Regents of the University of California

  公开号：US20200197534A1

  公开（公告）日：2020-06-25

  In certain embodiments a platform technology for the facilitating immune therapy in the treatment of cancer is provided. In certain embodiments nanocarriers are provided that facilitate delivery of an IDO inhibitor in conjunction with an inducer of cell death (ICD-inducer). In certain embodiments the IDO inhibitor is conjugated to a component of a lipid bilayer forming a nanovesicle. In still another embodiment, methods and compositions are provided where an ICD-inducing agent (e.g., doxorubicin, oxaliplatin, mitoxantrone etc.) and an IDO pathway inhibitor (e.g., an IDO inhibitor-prodrug) are integrated into a nanocarrier (e.g. a lipid-bilayer (LB)-coated nanoparticle), that allows systemic delivery to orthotopic pancreatic cancer site.

  在某些实施例中，提供了一种用于促进免疫疗法治疗癌症的平台技术。在某些实施例中，提供了一种纳米载体，可促进与细胞死亡诱导剂（ICD诱导剂）一起传递IDO抑制剂。在某些实施例中，IDO抑制剂与脂质双层的组分结合形成纳米囊泡。在另一实施例中，提供了一种方法和组合物，其中ICD诱导剂（例如多柔比星、奥沙利铂、米托蒽醌等）和IDO途径抑制剂（例如IDO抑制剂前药）被整合到一个纳米载体（例如脂质双层（LB）包被的纳米粒子）中，从而实现对原位胰腺癌部位的全身传递。
• Novel IDO Inhibitors and Methods of Use Thereof
  申请人：Prendergast George C.

  公开号：US20100166881A1

  公开（公告）日：2010-07-01

  Novel indoleamine 2,3-dioxygenase (IDO) inhibitors, compositions comprising the same, and methods of use thereof are disclosed.

  本发明揭示了新型的色氨酸2,3-双加氧酶（IDO）抑制剂、包含该抑制剂的组合物以及其使用方法。
• NOVEL IDO INHIBITORS AND METHODS OF USE THEREOF
  申请人：Lankenau Institute for Medical Research

  公开号：EP1940787A1

  公开（公告）日：2008-07-09
• EP1940787A4
  申请人：——

  公开号：EP1940787A4

  公开（公告）日：2009-07-01