1-bromoocta-7-yn-2-one | 1219915-42-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-bromoocta-7-yn-2-one
• 英文别名: 1-Bromooct-7-yn-2-one
• CAS: 1219915-42-0
• 化学式: C₈H₁₁BrO
• 分子量: 203.079
• InChiKey: BKRMITHAUPYGQH-UHFFFAOYSA-N

物化性质

• 沸点：
  269.7±20.0 °C(Predicted)
• 密度：
  1.313±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-bromoocta-7-yn-2-one 、 N-[(tert-butoxy)carbonyl]-L-cysteine methyl ester 在 N,N-二异丙基乙胺 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以78%的产率得到
  参考文献：
  名称：

  A Caged Electrophilic Probe for Global Analysis of Cysteine Reactivity in Living Cells

  摘要：

  Cysteine residues are subject to diverse modifications, such as oxidation, nitrosation, and lipidadon. The resulting loss in cysteine reactivity can be measured using electrophilic chemical probes, which importantly provide the stoichiometry of modification. An iodoacetamide (IA)-based chemical probe has been used to concurrently quantify reactivity changes in hundreds of cysteines within cell lysates. However, the cytotoxicity of the IA group precludes efficient live-cell labeling, which is important for preserving transient cysteine modifications. To overcome this limitation, a caged bromomethyl ketone (BK) electrophile was developed, which shows minimal cytotoxicity and provides spatial and temporal control of electrophile activation through irradiation. The caged-BK probe was utilized to monitor cysteine reactivity changes in A431 cells upon epidermal growth factor (EGF)-stimulated release of cellular reactive oxygen species. Decreased reactivity was observed for cysteines known to form sulfenic acids and redox-active disulfides. Importantly, the caged-BK platform provided the first quantification of intracellular disulfide bond formation upon EGF stimulation. In summary, the caged-BK probe is a powerful tool to identify reactivity changes associated with diverse cysteine modifications, including oxidation, metal chelation, and inhibitor binding, within a physiologically relevant context.

  DOI：

  10.1021/jacs.5b04350
• 作为产物：
  描述：

  6-庚炔酸 在 草酰氯 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 4.17h， 生成 1-bromoocta-7-yn-2-one
  参考文献：
  名称：

  A Caged Electrophilic Probe for Global Analysis of Cysteine Reactivity in Living Cells

  摘要：

  Cysteine residues are subject to diverse modifications, such as oxidation, nitrosation, and lipidadon. The resulting loss in cysteine reactivity can be measured using electrophilic chemical probes, which importantly provide the stoichiometry of modification. An iodoacetamide (IA)-based chemical probe has been used to concurrently quantify reactivity changes in hundreds of cysteines within cell lysates. However, the cytotoxicity of the IA group precludes efficient live-cell labeling, which is important for preserving transient cysteine modifications. To overcome this limitation, a caged bromomethyl ketone (BK) electrophile was developed, which shows minimal cytotoxicity and provides spatial and temporal control of electrophile activation through irradiation. The caged-BK probe was utilized to monitor cysteine reactivity changes in A431 cells upon epidermal growth factor (EGF)-stimulated release of cellular reactive oxygen species. Decreased reactivity was observed for cysteines known to form sulfenic acids and redox-active disulfides. Importantly, the caged-BK platform provided the first quantification of intracellular disulfide bond formation upon EGF stimulation. In summary, the caged-BK probe is a powerful tool to identify reactivity changes associated with diverse cysteine modifications, including oxidation, metal chelation, and inhibitor binding, within a physiologically relevant context.

  DOI：

  10.1021/jacs.5b04350

文献信息

• Synthesis and Antitumor Activity of a Novel Series of 6-Substituted Pyrrolo[2,3-<i>d</i>]pyrimidine Thienoyl Antifolate Inhibitors of Purine Biosynthesis with Selectivity for High Affinity Folate Receptors and the Proton-Coupled Folate Transporter over the Reduced Folate Carrier for Cellular Entry
  作者：Lei Wang、Christina Cherian、Sita Kugel Desmoulin、Lisa Polin、Yijun Deng、Jianmei Wu、Zhanjun Hou、Kathryn White、Juiwanna Kushner、Larry H. Matherly、Aleem Gangjee

  DOI：10.1021/jm9015729

  日期：2010.2.11

  ituted pyrrolo[2,3-d]pyrimidines with a thienoyl side chain and four to six carbon bridge lengths (compounds 1−3) were synthesized as substrates for folate receptors (FRs) and the proton-coupled folate transporter (PCFT). Conversion of acetylene carboxylic acids to α-bromomethylketones and condensation with 2,4-diamino-6-hydroxypyrimidine afforded the 6-substituted pyrrolo[2,3-d]pyrimidines. Sonogashira

  合成了具有噻吩酰基侧链和 4 到 6 个碳桥长度的2-氨基-4-氧代-6-取代的吡咯并[2,3- d ]嘧啶（化合物1 - 3）作为叶酸受体 (FR) 的底物和质子偶联叶酸转运蛋白 (PCFT)。乙炔羧酸转化为α-溴甲基酮并与2,4-二氨基-6-羟基嘧啶缩合得到6-取代的吡咯并[2,3- d ]嘧啶。薗头与（耦合小号）-2 - [（5-溴-噻吩-2-羰基） -氨基] -戊二酸二乙酯，随后氢化和皂化，得到1 - 3。化合物1和2有效抑制表达 FRα、减少叶酸载体 (RFC) 和 PCFT 的 KB 和 IGROV1 人类肿瘤细胞。类似物对 FR 和 PCFT 比 RFC 具有选择性。甘氨酰胺核糖核苷酸甲酰转移酶是主要的细胞靶标。在具有 KB 肿瘤的 SCID 小鼠中，1对早期（3.5 log 杀死，1/5 治愈）和晚期（3.7 log 杀死，4/5 完全缓解）阶段的肿瘤具有高度活性。我们的结果表明，由于
• A Caged Electrophilic Probe for Global Analysis of Cysteine Reactivity in Living Cells
  作者：Masahiro Abo、Eranthie Weerapana

  DOI：10.1021/jacs.5b04350

  日期：2015.6.10

  Cysteine residues are subject to diverse modifications, such as oxidation, nitrosation, and lipidadon. The resulting loss in cysteine reactivity can be measured using electrophilic chemical probes, which importantly provide the stoichiometry of modification. An iodoacetamide (IA)-based chemical probe has been used to concurrently quantify reactivity changes in hundreds of cysteines within cell lysates. However, the cytotoxicity of the IA group precludes efficient live-cell labeling, which is important for preserving transient cysteine modifications. To overcome this limitation, a caged bromomethyl ketone (BK) electrophile was developed, which shows minimal cytotoxicity and provides spatial and temporal control of electrophile activation through irradiation. The caged-BK probe was utilized to monitor cysteine reactivity changes in A431 cells upon epidermal growth factor (EGF)-stimulated release of cellular reactive oxygen species. Decreased reactivity was observed for cysteines known to form sulfenic acids and redox-active disulfides. Importantly, the caged-BK platform provided the first quantification of intracellular disulfide bond formation upon EGF stimulation. In summary, the caged-BK probe is a powerful tool to identify reactivity changes associated with diverse cysteine modifications, including oxidation, metal chelation, and inhibitor binding, within a physiologically relevant context.