ethyl 2-(4-isothiocyanatophenyl)acetate | 22676-74-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 2-(4-isothiocyanatophenyl)acetate
• 英文别名: Ethyl 2-(4-isothiocyanatophenyl)acetate
• CAS: 22676-74-0
• 化学式: C₁₁H₁₁NO₂S
• 分子量: 221.28
• InChiKey: QEBRCXKNRYGSOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  70.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-(4-isothiocyanatophenyl)acetate 、 2,3-二氨基甲苯 在 carbodiimide reagent 作用下， 以 二氯甲烷 为溶剂， 反应 16.5h， 生成
  参考文献：
  名称：

  Highly Potent, Water Soluble Benzimidazole Antagonist for Activated α₄β₁ Integrin

  摘要：

  The cell surface receptor alpha(4)beta(1), integrin, activated constitutively in lymphoma, can be targeted with the bisaryl urea peptidomimetic antagonist 1 (LLP2A). However, concerns on its preliminary pharmacokinetc (PK) profile provided an impetus to change the pharmacophore from a bisaryl urea to a 2-arylaminobenzimidazole moiety, resulting in improved solubility while maintaining picomolar potency [5 (KLCA4); IC50 = 305 pM]. With exceptional solubility, this finding has the potential for improving PK to help diagnose and treat lymphomas.

  DOI：

  10.1021/jm070790o
• 作为产物：
  描述：

  硫光气 、 4-氨基苯乙酸乙酯 在 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 反应 12.5h， 以93%的产率得到ethyl 2-(4-isothiocyanatophenyl)acetate
  参考文献：
  名称：

  Highly Potent, Water Soluble Benzimidazole Antagonist for Activated α₄β₁ Integrin

  摘要：

  The cell surface receptor alpha(4)beta(1), integrin, activated constitutively in lymphoma, can be targeted with the bisaryl urea peptidomimetic antagonist 1 (LLP2A). However, concerns on its preliminary pharmacokinetc (PK) profile provided an impetus to change the pharmacophore from a bisaryl urea to a 2-arylaminobenzimidazole moiety, resulting in improved solubility while maintaining picomolar potency [5 (KLCA4); IC50 = 305 pM]. With exceptional solubility, this finding has the potential for improving PK to help diagnose and treat lymphomas.

  DOI：

  10.1021/jm070790o

文献信息

• Synthesis of Isothiocyanates from Primary Amines via Visible-Light Photocatalysis
  作者：Jinglin Ma、Fengxi Li、Chunyu Wang、Zhi Wang、Chuang Du、Lei Wang

  DOI：10.1021/acs.orglett.3c02193

  日期：2023.8.4

  A photocatalyzed, efficient, and mild approach for the synthesis of various substituted isothiocyanates from amine and carbon disulfide was reported in this work. This approach expands the scope of photocatalytic applications and provides a new method for the preparation of aliphatic and aromatic isothiocyanates, which are significant organic building blocks and biological diagnostic markers.

  这项工作报道了一种光催化、高效且温和的方法，用于从胺和二硫化碳合成各种取代的异硫氰酸酯。这种方法扩大了光催化应用范围，并为制备脂肪族和芳香族异硫氰酸酯提供了一种新方法，脂肪族和芳香族异硫氰酸酯是重要的有机构件和生物诊断标记物。
• Selectively Targeting T- and B-Cell Lymphomas: A Benzothiazole Antagonist of α₄β₁ Integrin
  作者：Richard D. Carpenter、Mirela Andrei、Olulanu H. Aina、Edmond Y. Lau、Felice C. Lightstone、Ruiwu Liu、Kit S. Lam、Mark J. Kurth

  DOI：10.1021/jm800313f

  日期：2009.1.8

  Current cancer chemotherapeutic agents clinically deployed today are designed to be indiscriminately cytotoxic, however. achieving selective targeting of cancer malignancies would allow for improved diagnostic and chemotherapeutic tools. Integrin alpha(4)beta(1), a heterodimeric cell surface receptor, is believed to have a low-affinity conformation in resting normal lymphocytes and an activated high-affinity conformation in cancerous cells, specifically T- and B-cell lymphomas. This highly attractive yet poorly understood receptor has been selectively targeted with the bisaryl urea peptidomimetic antagonist 1. However. concerns regarding its preliminary pharmacokinetic (PK) profile provided an impetus to change the pharmacophore from a bisaryl urea to a 2-arylaminobenzothiazole moiety, resulting in an analogue with improved physicochemical properties, solubility, and kidney:tumor ratio while maintaining potency (6; IC50 = 53 pM). The results presented herein utilized heterocyclic and solid-phase chemistry, cell adhesion assay, and in vivo optical imaging using the cyanine dye Cy5.5 conjugate.
• 47. The inhibitory effect of substituents in chemical reactions. Part III. The reactivity of the isothiocyano-group in substituted arylthiocarbimides
  作者：Donald W. Browne、G. Malcolm Dyson

  DOI：10.1039/jr9340000178

  日期：——
• Kristian,P. et al., Collection of Czechoslovak Chemical Communications, 1969, vol. 34, p. 563 - 571
  作者：Kristian,P. et al.

  DOI：——

  日期：——
• Heterocyclic Ligands for Integrin Imaging and Therapy
  申请人：Carpenter Richard D.

  公开号：US20100310455A1

  公开（公告）日：2010-12-09

  The present invention provides α 4 β 1 integrin ligands that display high binding affinity, specificity, and stability. The ligands comprise a peptide having n independently selected amino acids, wherein at least one amino acid is an unnatural amino acid or a D-amino acid, and wherein n is an integer of from 3 to 20. Methods are provided for administering the ligands for treating cancer, inflammatory diseases, and autoimmune diseases. Also provided are methods for administering the ligands for imaging a tumor, organ, or tissue in a subject.