The Preparation and Reactions of 2-Alkyl-1-(or 3)-nitro-2-thiopseudourea. Part I. Reaction with Amines¹

Targeting nitric oxide synthase with 99mTc/Re-tricarbonyl complexes containing pendant guanidino or isothiourea moieties

“…L 2 was synthesized by reaction of the same precursor with cyanogen bromide, followed by hydroxyguanylation with hydroxylamine, and removal of the Boc-protecting group with TFA [23]. The synthesis of L 4 , which bears a pendant N-nitroguanidine group, was accomplished by nitroguanylation of the precursor compound with 2-methyl-1-nitro-2-thiopseudourea [24]. The S-methylisothiourea-containing conjugate L 5 was obtained as a side product in the preparation of L 4 .…”

Selective l-nitroargininylaminopyrrolidine and l-nitroargininylaminopiperidine neuronal nitric oxide synthase inhibitors

“…As originally reported, the reduction of the nitrile to an amine was first tried with PtO 2 -catalyzed hydrogenation in isopropanol in the presence of HCl. 19 Later we found that the nitrile reduction could be performed in a more facile and consistent manner by hydrogenation at 1 atmosphere pressure with Pd(OH) 2 /C as the catalyst in methanol/acetic acid (1:1) solution. The Pd(OH) 2 catalyst also is much cheaper than PtO 2 , propitious for a large scale reaction.…”

“…N α -Boc-N α -Methyl-L-ornithine (19) was synthesized according to a literature procedure 18 using a modification of the nitrile reduction method. The synthesis started with Boc-L-Gln-OH; the γ-carboxamide of Boc-L-Gln-OH was dehydrated to a nitrile using acetic anhydride and pyridine.…”

Synthesis and Structure-Activity Relationships of Dinotefuran Derivatives: Modification in the Nitroguanidine Part

“…Cyclic nitroimino and nitromethylene compounds (xi and xii) were prepared by condensation of diamines from (x) with (ii) or with S-methyl-N-nitro-NЈ-phthaloylisothiourea (v) (Method D). The (tetra-hydro-3-furyl)methyl derivatives (i and x 5) ) and the isothiourea derivatives (v 18) and viii 19) ) were prepared according to established procedures. Typical synthetic procedures are described as follows.…”

“…The acyclic nitroimino compounds (14)(15)(16)(17)(18)(19)(20)(21)(22) and the acyclic nitromethylene compounds (5-13) are similar in SAR and activity level. Both derivatives have the same clear trend for decreased activity with increasing size of the N-alkyl substituents.…”