4-(acetoxy)benzyl chloroformate | 86157-54-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 4-(acetoxy)benzyl chloroformate
• 英文别名: 4-(((chlorocarbonyl)oxy)methyl)phenyl acetate；[4-(Carbonochloridoyloxymethyl)phenyl] acetate
• CAS: 86157-54-2
• 化学式: C₁₀H₉ClO₄
• 分子量: 228.632
• InChiKey: AGNXJOKAPDWCLT-UHFFFAOYSA-N

物化性质

• 沸点：
  311.5±35.0 °C(Predicted)
• 密度：
  1.308±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(acetoxy)benzyl chloroformate 在 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 13.0h， 生成
  参考文献：
  名称：

  Chemoenzymatic Synthesis of N-Ras Lipopeptides

  摘要：

  For the study of biological phenomena influenced by the plasma-membrane-bound Ras proteins and other lipidated proteins, characteristic peptides which embody the correct lipid modifications of their parent proteins (palmitoyl thioesters and farnesyl thioethers), as well as analogues thereof, may serve as suitable tools. For the construction of such acid- and base-labile peptide conjugates, the enzyme-labile p-acetoxybenzyloxycarbonyl (AcOZ) urethane blocking group was developed. The acetate moiety within the AcOZ group is easily saponified by treatment with acetyl esterase or lipase. After cleavage of the acetate group the resulting quinone methide spontaneously fragments, resulting in the liberation of the desired peptide or peptide conjugates. This enzymatic protecting group technique formed the key step in the synthesis of the characteristic S-palmitoylated and S-farnesylated C-terminus of the human N-Ras protein. Deprotections are so mild that no undesired side reactions of the lipid conjugates are observed (i.e., no hydrolysis or beta-elimination of the thioester and no acid-mediated attack on the double bonds of the farnesyl group). The combination of enzymatic protecting group techniques with classical chemical methods allowed access to various fluorescent-labeled and differently lipid-modified Rns lipopeptides. Their application in biological experiments enabeled the study of the structural requirements for the acylation of Ras sequence motifs in vivo and gave insight into the subcellular site at which these modifications occur. The results indicate that the plasma membrane is a major site of cellular S-acylation. This supports a mechanism for the selective subcellular localization of lipidated proteins, including the Rns proteins themselves, by kinetic targeting to the plasma membrane.

  DOI：

  10.1021/ja9805627
• 作为产物：
  描述：

  对羟基苯甲醇 在 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.92h， 生成 4-(acetoxy)benzyl chloroformate
  参考文献：
  名称：

  基于7-羟基-2-亚氨基香豆素支架的原位形成的双重酶促响应“开启”荧光传感系统†

  摘要：

  描述了同时荧光检测两种不同酶活性的新策略，即水解酶（酰胺酶或酯酶）和还原酶。这种创新的生物传感方法基于强大的“共价组装”原理，涉及从无荧光笼状前体原位合成荧光团，并通过两种目标分析物触发的多米诺反应。为了建立这种方法，选择了青霉素G酰基转移酶（PGA）（或猪肝酯酶（PLE））和硝基还原酶（NTR）作为模型酶，并使用原始的bis- O合成了作为双反应探针的被保护的2，4-二羟基肉桂腈衍生物，当与两种选择的酶反应时，它们可以容易地转化为高荧光的7-羟基-2-亚氨基香豆素支架。这些探针的核心结构中可用的两个酚基团在分子内环化反应（C-2位置的羟基）产生亚氨基香豆素骨架并增强其推挽特性（C-4位置的羟基）方面起着关键作用。 ）。它们具有两个不同的对酶不稳定的掩蔽基团的正交保护和暂时保护，是这类新颖的荧光“开启”探针设计的基石。使用基于荧光的体外评估 分析和HPLC-荧光/ -MS分析使我们既能够证

  DOI：

  10.1039/c5ob01624j

文献信息

• Versatile approach to α-alkoxy carbamate synthesis and stimulus-responsive alcohol release
  作者：R. Adam Mosey、Paul E. Floreancig

  DOI：10.1039/c2ob26571k

  日期：——

  A series of α-alkoxy carbamates that cleave under mild conditions to release alcohols has been synthesized through a multicomponent process. The relationship between structural features in these compounds and the rate of alcohol release in the presence of basic hydrogen peroxide has been studied. The preparation of carbamates that cleave under other conditions has been demonstrated.

  一系列 α-烷氧基氨基甲酸酯在温和条件下裂解以释放醇，已通过多组分工艺合成。这些化合物的结构特征与碱性物质存在下醇释放速率之间的关系过氧化氢已被研究。在其他条件下裂解的氨基甲酸酯的制备已得到证实。
• Synthesis and Biological Evaluation of Lipophilic Nucleoside Analogues as Inhibitors of Aminoacyl-tRNA Synthetases
  作者：Manesh Nautiyal、Bharat Gadakh、Steff De Graef、Luping Pang、Masroor Khan、Yi Xun、Jef Rozenski、Arthur Van Aerschot

  DOI：10.3390/antibiotics8040180

  日期：——

  aminoacyl-tRNA synthetase (aaRSs) could be one such target for the development of antibiotics. The aaRSs are a group of enzymes that catalyze the transfer of an amino acid to their cognate tRNA and therefore play a pivotal role in translation. Thus, selective inhibition of these enzymes could be detrimental to microbes. The 5'-O-(N-(L-aminoacyl)) sulfamoyladenosines (aaSAs) are potent inhibitors of the respective

  病原菌中新出现的抗生素抗药性和现有抗生素发现管道中化合物的减少是医疗保健专业人员最为关注的问题。潜在的解决方案旨在探索新的或现有的目标/化合物。抑制细菌氨酰基-tRNA合成酶（aaRSs）可能是开发抗生素的目标之一。aaRSs是一组酶，可催化氨基酸转移至同源tRNA，因此在翻译中起关键作用。因此，对这些酶的选择性抑制可能对微生物有害。5'-O-（N-（L-氨基酰基））磺​​酰胺基腺苷（aaSAs）是相应aaRS的有效抑制剂，但是由于它们的极性和带电性质，它们无法穿过细菌膜。在这项工作中 我们增加了这些现有aaSA的亲脂性，以促进它们通过细菌膜的渗透。遵循两种策略，要么通过N6-位的烷基化在腺嘌呤环上连接一个（永久性）烷基部分，要么在α-末端胺基上引入一个亲脂性可生物降解的前药部分，总共有八个新的aaSA类似物。使用纯化的大肠杆菌aaRS酶或在从大肠杆菌获得的总细胞提取物中，对所有合成的化合
• Prodrugs of PKC modulators show enhanced HIV latency reversal and an expanded therapeutic window
  作者：Jack L. Sloane、Nancy L. Benner、Katherine N. Keenan、Xiaoyu Zang、Mohamed S. A. Soliman、Xiaomeng Wu、Melanie Dimapasoc、Tae-Wook Chun、Matthew D. Marsden、Jerome A. Zack、Paul A. Wender

  DOI：10.1073/pnas.1919408117

  日期：2020.5.19

  Since the start of the HIV/AIDS epidemic, approximately 32 million people have died from the infection. Although antiretroviral therapy slows disease progression by preventing virus replication, it does not eliminate latently infected cells, which can resupply active virus, necessitating lifelong treatment. Latency-reversing agents (LRAs), such as protein kinase C (PKC) modulators, present a strategy to cure the disease by activating and enabling immunological clearance of latent viral reservoirs. A major challenge with the clinical use of LRAs is sustaining therapeutic levels of the active agent while minimizing side effects. To address this problem, we report prodrugs of PKC modulators for use in HIV eradication. Relative to the parent, select prodrugs show delayed activation and significantly better efficacy and tolerability.

  《意义》自HIV/AIDS流行开始以来，大约有3200万人死于这种感染。尽管抗逆转录病毒疗法通过阻止病毒复制减缓疾病进展，但它并不能消除潜伏感染的细胞，这些细胞可以重新供应活跃病毒，需要终身治疗。潜伏病毒激活剂（LRAs），如蛋白激酶C（PKC）调节剂，提出了通过激活并促使潜在病毒储库的免疫清除来治愈疾病的策略。临床使用LRAs面临的主要挑战是在最小化副作用的同时维持活性药物的治疗水平。为了解决这个问题，我们报告了PKC调节剂的前药，用于HIV根除。与母药相比，选择性前药显示出延迟激活和显著更好的疗效和耐受性。
• [EN] LOW MOLECULAR WEIGHT PROTEIN DEGRADERS AND THEIR APPLICATIONS<br/>[FR] AGENTS DE DÉGRADATION DE PROTÉINES DE FAIBLE POIDS MOLÉCULAIRE ET LEURS APPLICATIONS
  申请人：CAPTOR THERAPEUTICS S A

  公开号：WO2022029138A1

  公开（公告）日：2022-02-10

  The invention relates to compounds of formulae (Ia), (Ib), (Ic) and (II) and their use in methods of treating cancer. The compounds may be applied in combination with already existing cancer-fighting regimens to increase their effectiveness.

  本发明涉及式(Ia)、(Ib)、(Ic)和(II)的化合物及其在治疗癌症方法中的应用。这些化合物可以与已有的抗癌疗法结合使用，以增加其疗效。
• PHOSPHONATED RIFAMYCINS AND USES THEREOF FOR THE PREVENTION AND TREATMENT OF BONE AND JOINT INFECTIONS
  申请人：Dietrich Evelyne

  公开号：US20110178001A1

  公开（公告）日：2011-07-21

  The present invention relates to phosphonated Rifamycins, and methods of making and using such compounds. These compounds are useful as antibiotics for prophylaxis and/or the treatment of bone and joint infections, especially for the prophylaxis and/or treatment of osteomyelitis.

  本发明涉及磷酸化利福霉素，以及制备和使用这些化合物的方法。这些化合物可用作抗生素，用于预防和/或治疗骨骼和关节感染，特别是用于预防和/或治疗骨髓炎。