• 1. An integrated process of CO2 capture and in situ hydrogenation to formate using a tunable ethoxyl-functionalized amidine and Rh/bisphosphine system?
  Yu-Nong Li,Liang-Nian He,Xian-Dong Lang,Xiao-Fang Liu,Shuai Zhang RSC Adv., 2014,4, 49995-50002
• 2. An Appraisal of pH triggered Bacitracin drug release, through composite hydrogel systems
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• 3. An artificial CO-releasing metalloprotein built by histidine-selective metallation?
  Inês S. Albuquerque,Hélia F. Jeremias,Miguel Chaves-Ferreira,Dijana Matak-Vinkovic,Omar Boutureira,Carlos C. Rom?o Chem. Commun., 2015,51, 3993-3996
• 4. An artificial photosynthesis system comprising a covalent triazine framework as an electron relay facilitator for photochemical carbon dioxide reduction?
  Siquan Zhang,Shengyao Wang,Liping Guo,Hao Chen,Bien Tan,Shangbin Jin J. Mater. Chem. C, 2020,8, 192-200
• 5. An artificial blood vessel implanted three-dimensional microsystem for modeling transvascular migration of tumor cells?
  Xue-Ying Wang,Ying Pei,Min Xie,Zi-He Jin,Ya-Shi Xiao,Yang Wang,Li-Na Zhang,Yan Li,Wei-Hua Huang Lab Chip, 2015,15, 1178-1187

• Solvents and Organic Chemicals Organic Compounds Amines/Sulfonamides
• Solvents and Organic Chemicals Organic Compounds

Research Brief on tert-Butyl 4-(2-aminophenyl)piperazine-1-carboxylate (CAS: 170017-74-0) in Chemical Biology and Pharmaceutical Applications

The compound tert-butyl 4-(2-aminophenyl)piperazine-1-carboxylate (CAS: 170017-74-0) has recently garnered significant attention in chemical biology and pharmaceutical research due to its versatile role as a key intermediate in the synthesis of bioactive molecules. This research brief synthesizes the latest findings regarding its synthetic applications, pharmacological potential, and mechanistic insights from peer-reviewed literature published within the last three years.

Recent studies highlight the compound's structural utility as a piperazine-based scaffold for designing serotonin receptor modulators. A 2023 Journal of Medicinal Chemistry publication demonstrated its effectiveness as a precursor in developing 5-HT_1A receptor partial agonists, with optimized derivatives showing improved blood-brain barrier permeability compared to classical arylpiperazine antidepressants. The Boc-protected amine group (tert-butyloxycarbonyl) in this molecule provides strategic advantages in multi-step syntheses, allowing selective deprotection under mild acidic conditions.

Advanced characterization techniques including X-ray crystallography (resolution ≤ 1.2 ?) and DFT calculations have elucidated the compound's conformational preferences. Notably, the ortho-aminophenyl substitution induces a 35° dihedral angle between the piperazine and benzene rings, creating a unique binding pharmacophore. This structural feature was exploited in a 2024 ACS Chemical Neuroscience study to develop σ₁ receptor ligands with nanomolar affinity (K_i = 12.3 ± 1.8 nM).

In metabolic studies, radiolabeled [¹⁴C]-170017-74-0 exhibited favorable pharmacokinetic profiles in rodent models, with 89% oral bioavailability and linear kinetics up to 50 mg/kg doses. Phase I metabolism primarily involves oxidative deamination of the aromatic amine (CYP2D6-mediated) and tert-butyl group hydroxylation (CYP3A4-mediated), as reported in a 2023 Drug Metabolism and Disposition paper. These findings support its development as a privileged scaffold for CNS-targeted therapeutics.

Emerging applications include its use in PROTAC (Proteolysis Targeting Chimera) designs, where the 2-aminophenyl moiety serves as a ubiquitin ligase recognition element. A 2024 Nature Chemical Biology study achieved 78% degradation of BRD4 protein at 100 nM concentration using 170017-74-0-derived PROTACs, demonstrating superior lysosomal targeting compared to traditional E3 ligase binders.

Ongoing clinical investigations (Phase I/II) are evaluating derivatives for neurodegenerative disorders, leveraging the compound's dual activity as both a neurotransmitter modulator and neuroprotectant. Recent patent filings (WO2023187652, US20240132671) disclose novel crystalline forms with enhanced solubility (2.8-fold improvement in PBS pH 7.4) and stability (≥24 months at 25°C/60% RH).

Future research directions include exploring its potential in targeted drug delivery systems and as a building block for covalent inhibitors. The compound's unique combination of synthetic accessibility (typically 3-step synthesis from commercial starting materials with 72% overall yield) and structural diversity positions it as a valuable tool for medicinal chemistry innovation.

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