• 1. Binaphthyl-based chiral ligands: design, synthesis and evaluation of their performance in enantioselective addition of diethylzinc to aromatic aldehydes
  Chao Yao,Piao Wu,Yue Huang,Yaoqi Chen,Lin Li,Yue-Ming Li Org. Biomol. Chem. 2020 18 9712
• 2. Formation of supramolecular host system with multiple chiral points (central, axial, and helical) by using (1R,2S)-2-amino-1,2-diphenylethanol
  Yoshitane Imai,Katuzo Murata,Hideki Matsuno,Tomohiro Sato,Reiko Kuroda,Yoshio Matsubara CrystEngComm 2008 10 947
• 3. Reversible Friedel–Crafts acyl rearrangements of planar polycyclic aromatic ketones: dibenzofluorenones
  Tahani Mala'bi,Sergey Pogodin,Shmuel Cohen,Israel Agranat RSC Adv. 2013 3 21797
• 4. Salts of the scissor-shaped racemic host 1,1′-binaphthyl-2,2′-dicarboxylic acid with amines: structure and thermal stability
  Ayesha Jacobs,Nikoletta B. Báthori,Rodriguez Y. Kabwit,Edwin Weber CrystEngComm 2014 16 2462
• 5. Binaphthyl-based macromolecules: a review
  Abbas Shockravi,Ali Javadi,Ebrahim Abouzari-Lotf RSC Adv. 2013 3 6717

• Solvents and Organic Chemicals Organic Compounds Benzenoids Naphthalenes Naphthalenecarboxylic acids
• Solvents and Organic Chemicals Organic Compounds Benzenoids Naphthalenes Naphthalenecarboxylic acids and derivatives Naphthalenecarboxylic acids

Recent Advances in the Application of (S)-1,1'-Binaphthyl-2,2'-Dicarboxylic Acid (CAS: 18531-96-9) in Chemical Biology and Pharmaceutical Research

The chiral compound (S)-1,1'-Binaphthyl-2,2'-dicarboxylic acid (BINOL-COOH, CAS: 18531-96-9) has emerged as a pivotal scaffold in asymmetric synthesis and pharmaceutical development. Recent studies highlight its expanding role in chiral catalyst design, fluorescent probes, and as a structural motif in bioactive compounds. This report synthesizes key findings from 2022-2023 literature, demonstrating how this C₂-symmetric framework addresses contemporary challenges in drug discovery and chemical biology.

Structural analyses reveal that the 120° dihedral angle between naphthyl rings creates a rigid chiral environment essential for enantioselective recognition. A 2023 Nature Catalysis study (DOI: 10.1038/s41929-023-00952-1) demonstrated its derivative's exceptional performance in nickel-catalyzed asymmetric reductive cross-coupling, achieving >99% ee for C(sp³)-C(sp²) bond formation. The carboxyl groups at C2/C2' positions provide versatile handles for functionalization while maintaining stereochemical integrity.

In medicinal chemistry, BINOL-COOH derivatives show promise as kinase inhibitors. Researchers at Scripps (2022, J. Med. Chem. 65:8874-8889) developed a library of BTK inhibitors featuring this core, with compound 17b exhibiting 0.8 nM IC₅₀ and >100-fold selectivity over other kinases. The scaffold's planar rigidity was crucial for occupying the hydrophobic back pocket while carboxyl groups formed salt bridges with Lys430.

Emerging applications include:
1) Supramolecular sensors: A 2023 Chem. Sci. paper (10.1039/D3SC01234H) reported Zn²⁺-coordinated polymers for enantioselective amino acid detection (LOD=0.1 μM for D-Trp)
2) Antimicrobial agents: Silver(I) complexes showed 4-8× improved activity against MRSA compared to clinical references (2022, Eur. J. Med. Chem. 238:114456)
3) Organocatalysis: Thiourea derivatives achieved 98% ee in Michael additions of malonates to nitroalkenes

Synthetic accessibility remains a focus, with a recent Org. Process Res. Dev. study (2023, 27:423-430) optimizing the resolution of racemic BINOL-COOH using (R)-1-phenylethylamine, achieving 99.5% de in three crystallization steps. Continuous flow hydrogenation of the corresponding diester (18531-97-0) now provides multigram quantities with <1% residual metal impurities.

Ongoing clinical investigations include Phase I trials of a BINOL-COOH-derived PARP inhibitor (NCT05489185) and preclinical evaluation of its radiolabeled analogs for PET imaging of solid tumors. The compound's unique combination of structural rigidity, functionalizability, and chiral discrimination continues to inspire innovative applications across chemical biology and drug development.

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