Synthesis and Structures of 9-Oxabispidine Analogues of Cisplatin, Carboplatin, and Oxaliplatin

Abstract

The literature synthesis of 9-oxabispidine [OC6H10(NH)2, C] has been revisited and optimized, which includes determination of the crystal structures of C, the secondary component trans-(PhSO2)NC4H6O(CH2I)2 (trans-III), and the unexpected solute intermediate OC6H10(NSO2Ph)2·(1)/2py (V·(1)/2py). The reaction of (1,5-hexadiene)platinum dichloride with C yields {OC6H10(NH)2}PtCl2 (C1), which is converted to {OC6H10(NH)2}Pt(cbdca)·5H2O (C2) and {OC6H10(NH)2}Pt(C2O4) (C3). In the crystal, C1 forms a planar 2D network by N-H··Cl and N-H··O hydrogen bonding. In the crystal structure of C2, which is isomorphous to the parent bispidine compound (A2), all complex molecules are encapsulated by a water shell. While complexes C1 and C3 are virtually insoluble in water, C2 dissolves quite well. The low cytotoxicity of compounds C1-C3 is explained by an increased polarity of the bonds in the C skeleton as a consequence of the electronegative O atom.

Ni(II), Pd(II), and Pt(II) Complexes of the Hedgehog Pathway Inhibitor GANT61-D

“…Selected bond lengths and bond angles around the Pt­(II) center can be seen in Tables and , respectively. The metal-centered Pt–N (2.033 and 2.027 Å) and Pt–O (2.020 and 2.024 Å) bond lengths are similar and comparable to the few literature examples of N-donor Pt­(CBDCA) (CBDCA = 1,1-cyclobutanedicarboxylic acid) complexes. − In 4 , the chelate amino groups form intramolecular hydrogen bonds with the N atoms of the NMe 2 groups, N15···N23 [ d (D···A) = 2.925(5) Å], as seen in complexes 2 and 3 .…”

Development of a novel carboplatin like cytoplasmic trackable near infrared fluorophore conjugate via strain-promoted azide alkyne cycloaddition

“…[25,26] The chelated cyclobutane dicarboxylate ligand geometry is similar to literature values. [27][28][29][30] The complex in 2 forms hydrogen bonded dimers with 4 N-H…O interactions. The molecules lie parallel over an inversion centre with a Pt…Pt distance of 3.1201(2) Å.…”

Synthesis, structural investigations, and cytotoxic evaluation of a half‐sandwich Ru(II)‐arene complex

“…Cisplatin and the follow‐up platinum‐based metallodrugs (carboplatin and oxaliplatin) have been successfully used as first‐line treatment regimens against diverse type of cancers including testicular, ovarian, and colorectal cancers. [ 1–3 ] However, despite the high efficacy of these platinum‐based drugs against different cancer phenotypes, their clinical use is seriously impeded by severe side effects and intrinsic resistance issues. [ 4,5 ] Among the potential alternatives of platinum‐based chemotherapeutics are the next generation ruthenium complexes that have demonstrated significant antineoplastic and antimetastatic properties besides exhibiting lower systemic toxicity and drug resistance.…”