m-trimethylsilylbenzyl cyanide | 5206-56-4

• 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: m-trimethylsilylbenzyl cyanide
• 英文别名: m-Trimethylsilylbenzylcyanide；3-Trimethylsilyl-benzylcyanid；2-(3-trimethylsilylphenyl)acetonitrile
• CAS: 5206-56-4
• 化学式: C₁₁H₁₅NSi
• 分子量: 189.332
• InChiKey: WYQSXFDQLRCSKQ-UHFFFAOYSA-N

物化性质

• 沸点：
  270.7±15.0 °C(Predicted)
• 密度：
  0.94±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  m-trimethylsilylbenzyl cyanide 在 sodium hydroxide 、 氯化亚砜 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 m-trimethylsilylphenylacetic acid chloride
  参考文献：
  名称：

  Studies on the Synthesis and Biological Properties of Non-Carrier-Added [¹²⁵I and ¹³¹I]-Labeled Arylalkylidenebisphosphonates:  Potent Bone-Seekers for Diagnosis and Therapy of Malignant Osseous Lesions

  摘要：

  Arylalkylidenebisphosphonates labeled with nca [I-125 or I-131] have been synthesized and their biological function investigated. The label was attached to the aromatic group in high yield and under mild conditions by means of iododesilylation. The bone affinities of the radioactive compounds were investigated in normal Balb/C mice. The compound 1-hydroxy(m-iodo[I-125,I-131]- phenylethylidene)-1,1-bisphosphonate was found to possess superior bone affinity compared to others, and its in vivo deiodination was insignificant. The uptake in femur 24h after injection was 850 +/- 265% and 986 +/- 118% of injected dose per gram tissue times gram body weight in mice and rats, respectively. The therapeutic potential of the compound was investigated in two tumor models in athymic (nude) rats, one model for mixed lytic/sclerotic metastatic bonelesions originating from breast cancer and the other model simulating osseous osteosarcoma. The effects in these models compare favorably to those observed for established treatment modalities. The experiments demonstrate that radioiodinated bisphosphonates may have a potential for diagnosis and therapy of malignant osseous lesions.

  DOI：

  10.1021/jm021107v
• 作为产物：
  描述：

  三甲基-(3-甲基苯基)硅烷 在 N-溴代丁二酰亚胺(NBS) 、 lithium hydroxide 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 N,N-二甲基甲酰胺 为溶剂， 生成 m-trimethylsilylbenzyl cyanide
  参考文献：
  名称：

  通过合理的碳硅生物等排替代策略鉴定出新型杀螨剂含硅吡唑基丙烯腈衍生物

  摘要：

  鉴定性能改进的新型吡唑基丙烯腈杀螨剂对于防治植食性螨具有重要价值。通过应用生物电子等排碳硅置换策略，合理设计了一系列创新的含硅吡唑基丙烯腈，并基于新颖的合成方法制备。经过研究，我们发现了具有出色杀螨活性的化合物A25 。化合物A25的 LC 50值为 0.062 mg/L，其效力分别是市售杀螨剂 cyenopyrafen 和 cyetpyrafen 的 2.3 倍和 1.9 倍。酶抑制试验表明，化合物A25的活性成分M1对朱砂叶螨SDH的IC 50值为2.32 μM ，比氰吡芬活性代谢物（IC 50 = 4.72 μM）高约两倍。分子对接研究表明，活性代谢物2和3及其相应的硅对应物与Trp165、Tyr433和Arg279残基形成氢键和阳离子-π相互作用。

  DOI：

  10.1021/acs.jafc.3c03898

文献信息

• Bis-phosphonate compounds
  申请人：——

  公开号：US06548042B2

  公开（公告）日：2003-04-15

  The present invention provides a pharmaceutical compound, or pharmaceutically acceptable salt thereof, for use in medicine, wherein said compound is of formula I wherein R is a pharmaceutically active moiety; Ar is an aromatic moiety; X is a linker group; and Y is a moiety comprising two phosphonate groups. Further aspects of the invention relate to a method for palliative and curative treatment of bone disorders and cancer related disorders, such as breast cancer.

  本发明提供了一种药物化合物，或其药用可接受的盐，用于医学上的使用，其中所述化合物为式I，其中R为药用活性基团；Ar为芳香基团；X为连接基团；Y为包含两个膦酸酯基团的基团。该发明的进一步方面涉及一种用于对骨骼疾病和癌症相关疾病（如乳腺癌）进行姑息治疗和治疗的方法。
• Rational Exploration of Novel SDHI Fungicide through an Amide-β-ketonitrile Bioisosteric Replacement Strategy
  作者：Cong Zhou、Xujuan Sun、Wen Fu、Zhong Li、Jiagao Cheng、Peter Maienfisch

  DOI：10.1021/acs.jafc.2c08606

  日期：——

  identification of succinate dehydrogenase inhibitor (SDHI) fungicides bearing a novel scaffold is of great importance to control pathogenic fungi. Difluoromethyl-pyrazole β-ketonitrile derivatives were rationally designed through an innovative amide-β-ketonitrile bioisosteric replacement strategy and evaluated for their antifungal activities. In preliminary fungicidal screening, our new β-ketonitrile compounds

  鉴定带有新型支架的琥珀酸脱氢酶抑制剂 (SDHI) 杀菌剂对于控制病原真菌具有重要意义。通过创新的酰胺-β-酮腈生物等排替代策略合理设计二氟甲基-吡唑 β-酮腈衍生物，并评估其抗真菌活性。在初步的杀菌筛选中，我们的新型 β-酮腈化合物显示出出色的体外活性。化合物A7和A14对核盘菌分别表现出 0.116 和 0.165 μg/mL 的 EC 50值，并且A14对丝核菌也表现出 0.0774 μg/mL 的 EC 50值。此外，A14对水稻纹枯病表现出适度的体内保护活性。SDH 酶促测定结果表明，A14对猪心脏 SDH 具有显着抑制作用，IC 50值为 0.183 μM，比 fluxapyroxad (IC 50 = 3.76 μM)强 20 倍。对接研究表明，氢键、阳离子-π 相互作用和边对面 π-π 相互作用在A14与R. solani SDH 的结合中起着关键作用。CoMSIA 模型指
• Studies on the Synthesis and Biological Properties of Non-Carrier-Added [¹²⁵I and ¹³¹I]-Labeled Arylalkylidenebisphosphonates:  Potent Bone-Seekers for Diagnosis and Therapy of Malignant Osseous Lesions
  作者：Erik Årstad、Per Hoff、Lars Skattebøl、Arne Skretting、Knut Breistøl

  DOI：10.1021/jm021107v

  日期：2003.7.1

  Arylalkylidenebisphosphonates labeled with nca [I-125 or I-131] have been synthesized and their biological function investigated. The label was attached to the aromatic group in high yield and under mild conditions by means of iododesilylation. The bone affinities of the radioactive compounds were investigated in normal Balb/C mice. The compound 1-hydroxy(m-iodo[I-125,I-131]- phenylethylidene)-1,1-bisphosphonate was found to possess superior bone affinity compared to others, and its in vivo deiodination was insignificant. The uptake in femur 24h after injection was 850 +/- 265% and 986 +/- 118% of injected dose per gram tissue times gram body weight in mice and rats, respectively. The therapeutic potential of the compound was investigated in two tumor models in athymic (nude) rats, one model for mixed lytic/sclerotic metastatic bonelesions originating from breast cancer and the other model simulating osseous osteosarcoma. The effects in these models compare favorably to those observed for established treatment modalities. The experiments demonstrate that radioiodinated bisphosphonates may have a potential for diagnosis and therapy of malignant osseous lesions.
• Novel Acaricidal Silico-Containing Pyrazolyl Acrylonitrile Derivatives Identified through Rational Carbon–Silicon Bioisosteric Replacement Strategy
  作者：Cong Zhou、Zhong Li、Xuhong Qian、Jiagao Cheng、Peter Maienfisch

  DOI：10.1021/acs.jafc.3c03898

  日期：2023.11.29

  The identification of novel pyrazolyl acrylonitrile acaricides with improved properties is of great value for the control of phytophagous mites. A series of innovative silicon-containing pyrazolyl acrylonitriles were rationally designed by applying a bioisosteric carbon–silicon replacement strategy and prepared based on novel synthetic methodology. As a result of our research, we discovered compound

  鉴定性能改进的新型吡唑基丙烯腈杀螨剂对于防治植食性螨具有重要价值。通过应用生物电子等排碳硅置换策略，合理设计了一系列创新的含硅吡唑基丙烯腈，并基于新颖的合成方法制备。经过研究，我们发现了具有出色杀螨活性的化合物A25 。化合物A25的 LC 50值为 0.062 mg/L，其效力分别是市售杀螨剂 cyenopyrafen 和 cyetpyrafen 的 2.3 倍和 1.9 倍。酶抑制试验表明，化合物A25的活性成分M1对朱砂叶螨SDH的IC 50值为2.32 μM ，比氰吡芬活性代谢物（IC 50 = 4.72 μM）高约两倍。分子对接研究表明，活性代谢物2和3及其相应的硅对应物与Trp165、Tyr433和Arg279残基形成氢键和阳离子-π相互作用。