[Bis(aminomethyl)dimethylsilane]platinum(II) dichloride: A potential antitumor agent

Abstract

Bis(aminomethyl)dimethylsilane]platinum(II) dichloride (1) was synthesized by a three-step procedure. The antitumor activity of 1 was evaluated in the i.p. implanted mouse L1210 leukemia model. A 10 mg kg-' dose administered every fourth day for a total of three injections extended the median life span of the dying mice by at least 100% and resulted in 40-50% survivors (day 30) in two experiments corresponding to an approximate 6 log,,, reduction in tumor burden at the end of treatment. Compound 1 appeared at least as active as cisplatin under the testing protocols utilized. The closely related bis[aminomethyltrimethylsilane]platinum(II) dichloride complex was inactive in this mouse model.

Silicon‐Containing Explosives: Syntheses and Sensitivity Studies of (Azidomethyl)‐, Bis(azidomethyl)‐, and Tris(azidomethyl)silanes

“…(Azidoalkyl)silanes of the formula type R 3 Si(CH 2 ) n N 3 ( n = 1–3) are known for decades 2. Due to serious explosions by distillation during the purification process, the explosive behavior of (azidomethyl)silanes was discovered early 3,4. They can serve as precursors in the synthesis of (aminomethyl)silanes, which have been used as ligands for the development of platinum‐based anticancer drugs 3–5…”

“…Thus, due to the covalent character of (azidomethyl)silanes, high sensitivities towards friction, impact, and thermal stimuli are to be expected for this class of compounds. And indeed, (azidomethyl)trimethylsilane ( 1b ), bis(azidomethyl)dimethylsilane ( 2b ), and tetrakis(azidomethyl)silane [Si(CH 2 N 3 ) 4 ] have been reported to be hazardous explosives 3,4,7…”

“…In continuation of our recently published study on a series of related (nitratomethyl)silanes,8 we have synthesized the (azidomethyl)silanes 1b–5b and have characterized these compounds systematically in terms of thermal stability as well as friction and impact sensitivity (Scheme ). The syntheses of 1b ,4,9 2b ,3,4 4b ,4 and 5b 5 have already been described elsewhere; however, in this study we have modified the synthetic methods.…”

Synthesis, antitumor activity, and chemical properties of silaplatin and related platinum(II) and platinum(IV) complexes derived from .beta.-silyl amines

“…Found: C, 15.09; H, 3.85; N, 6.81. The off-white solid was dissolved in DMSO and precipitated with water to give a light yellow solid (2.773 g, 40%) which was then purified twice by dissolution in DMF and precipitated slowly by the addition of ether to yield a crystal-like yellow solid (1.617 g, 23%): mp 241-247 °G (shrinks), 250 °C dec; NMR (DMF-d/TMS) 0.30 (s, 3 H, Si-CH3), 0.94 [(0.61-1.21) m, 5 H, Si-CH2-C + C-CH3], 2.45 (t br t, Jpwch = 27 Hz, Jhnch = 6 Hz, 4 H, Si-CH2-N), 4.86 (br t, JptNH = 39 Hz, 4 H, NH2); IR (KBr) 3217, 3138, 2951, 2879,1597,1437,1154 cm'1.…”

“…2 This report describes the synthesis and evaluation of platinum complexes derived from /3-silyl-substituted amines. 3 The effect of the silicon in the /3-position is one of a powerful electron-releasing substituent that can stabilize positively charged species through a hyperconjugative interaction (the so-called /3-effect of silicon). 4 The /3-effect increases the base strength of amines: 2,2dimethylaminopropane has a = 10.21 compared to f State University of New York at Buffalo.…”