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Indazole N-oxide derivatives as antiprotozoal agents: synthesis, biological evaluation and mechanism of action studies.char = A;code = 65 char = ;code = 32 char = s;code = 115 char = e;code = 101 char = r;code = 114 char = i;code = 105 char = e;code = 101 char = s;code = 115 char = ;code = 32 char = o;code = 111 char = f;code = 102 char = ;code = 32 char = i;code = 105 char = n;code = 110 char = d;code = 100 char = a;code = 97 char = z;code = 122 char = o;code = 111 char = l;code = 108 char = e;code = 101 char = ;code = 32 char = N;code = 78 char = -;code = 45 char = o;code = 111 char = x;code = 120 char = i;code = 105 char = d;code = 100 char = e;code = 101 char = ;code = 32 char = d;code = 100 char = e;code = 101 char = r;code = 114 char = i;code = 105 char = v;code = 118 char = a;code = 97 char = t;code = 116 char = i;code = 105 char = v;code = 118 char = e;code = 101 char = s;code = 115 char = ;code = 32 char = h;code = 104 char = a;code = 97 char = v;code = 118 char = e;code = 101 char = ;code = 32 char = b;code = 98 char = e;code = 101 char = e;code = 101 char = n;code = 110 char = ;code = 32 char = s;code = 115 char = y;code = 121 char = n;code = 110 char = t;code = 116 char = h;code = 104 char = e;code = 101 char = s;code = 115 char = i;code = 105 char = z;code = 122 char = e;code = 101 char = d;code = 100 char = ;code = 32 char = a;code = 97 char = n;code = 110 char = d;code = 100 char = ;code = 32 char = t;code = 116 char = h;code = 104 char = e;code = 101 char = i;code = 105 char = r;code = 114 char = ;code = 32 char = a;code = 97 char = n;code = 110 char = t;code = 116 char = i;code = 105 char = c;code = 99 char = h;code = 104 char = a;code = 97 char = g;code = 103 char = a;code = 97 char = s;code = 115 char = i;code = 105 char = c;code = 99 char = ;code = 32 char = a;code = 97 char = n;code = 110 char = d;code = 100 char = ;code = 32 char = l;code = 108 char = e;code = 101 char = i;code = 105 char = s;code = 115 char = h;code = 104 char = m;code = 109 char = a;code = 97 char = n;code = 110 char = o;code = 111 char = c;code = 99 char = i;code = 105 char = d;code = 100 char = a;code = 97 char = l;code = 108 char = ;code = 32 char = p;code = 112 char = r;code = 114 char = o;code = 111 char = p;code = 112 char = e;code = 101 char = r;code = 114 char = t;code = 116 char = i;code = 105 char = e;code = 101 char = s;code = 115 char = ;code = 32 char = s;code = 115 char = t;code = 116 char = u;code = 117 char = d;code = 100 char = i;code = 105 char = e;code = 101 char = d;code = 100 char = .;code = 46 char = ;code = 32 char = 3;code = 51 char = -;code = 45 char = C;code = 67 char = y;code = 121 char = a;code = 97 char = n;code = 110 char = o;code = 111 char = -;code = 45 char = 2;code = 50 char = -;code = 45 char = (;code = 40 char = 4;code = 52 char = -;code = 45 char = i;code = 105 char = o;code = 111 char = d;code = 100 char = o;code = 111 char = p;code = 112 char = h;code = 104 char = e;code = 101 char = n;code = 110 char = y;code = 121 char = l;code = 108 char = );code = 41 char = -;code = 45 char = 2;code = 50 char = H;code = 72 char = -;code = 45 char = i;code = 105 char = n;code = 110 char = d;code = 100 char = a;code = 97 char = z;code = 122 char = o;code = 111 char = l;code = 108 char = e;code = 101 char = ;code = 32 char = N;code = 78 char = 1;code = 49 char = -;code = 45 char = o;code = 111 char = x;code = 120 char = i;code = 105 char = d;code = 100 char = e;code = 101 char = ;code = 32 char = e;code = 101 char = x;code = 120 char = h;code = 104 char = i;code = 105 char = b;code = 98 char = i;code = 105 char = t;code = 116 char = e;code = 101 char = d;code = 100 char = ;code = 32 char = i;code = 105 char = n;code = 110 char = t;code = 116 char = e;code = 101 char = r;code = 114 char = e;code = 101 char = s;code = 115 char = t;code = 116 char = i;code = 105 char = n;code = 110 char = g;code = 103 char = ;code = 32 char = a;code = 97 char = n;code = 110 char = t;code = 116 char = i;code = 105 char = c;code = 99 char = h;code = 104 char = a;code = 97 char = g;code = 103 char = a;code = 97 char = s;code = 115 char = i;code = 105 char = c;code = 99 char = ;code = 32 char = a;code = 97 char = c;code = 99 char = t;code = 116 char = i;code = 105 char = v;code = 118 char = i;code = 105 char = t;code = 116 char = y;code = 121 char = ;code = 32 char = o;code = 111 char = n;code = 110 char = ;code = 32 char = t;code = 116 char = h;code = 104 char = e;code = 101 char = ;code = 32 char = t;code = 116 char = w;code = 119 char = o;code = 111 char = ;code = 32 char = p;code = 112 char = a;code = 97 char = r;code = 114 char = a;code = 97 char = s;code = 115 char = i;code = 105 char = t;code = 116 char = i;code = 105 char = c;code = 99 char = ;code = 32 char = s;code = 115 char = t;code = 116 char = r;code = 114 char = a;code = 97 char = i;code = 105 char = n;code = 110 char = s;code = 115 char = ;code = 32 char = a;code = 97 char = n;code = 110 char = d;code = 100 char = ;code = 32 char = t;code = 116 char = h;code = 104 char = e;code = 101 char = ;code = 32 char = t;code = 116 char = w;code = 119 char = o;code = 111 char = ;code = 32 char = p;code = 112 char = a;code = 97 char = r;code = 114 char = a;code = 97 char = s;code = 115 char = i;code = 105 char = t;code = 116 char = i;code = 105 char = c;code = 99 char = ;code = 32 char = s;code = 115 char = t;code = 116 char = a;code = 97 char = g;code = 103 char = e;code = 101 char = s;code = 115 char = ;code = 32 char = e;code = 101 char = v;code = 118 char = a;code = 97 char = l;code = 108 char = u;code = 117 char = a;code = 97 char = t;code = 116 char = e;code = 101 char = d;code = 100 char = .;code = 46 char = ;code = 32 char = F;code = 70 char = u;code = 117 char = r;code = 114 char = t;code = 116 char = h;code = 104 char = e;code = 101 char = r;code = 114 char = m;code = 109 char = o;code = 111 char = r;code = 114 char = e;code = 101 char = ,;code = 44 char = ;code = 32 char = b;code = 98 char = e;code = 101 char = s;code = 115 char = i;code = 105 char = d;code = 100 char = e;code = 101 char = s;code = 115 char = ;code = 32 char = i;code = 105 char = t;code = 116 char = s;code = 115 char = ;code = 32 char = t;code = 116 char = r;code = 114 char = y;code = 121 char = p;code = 112 char = a;code = 97 char = n;code = 110 char = o;code = 111 char = c;code = 99 char = i;code = 105 char = d;code = 100 char = a;code = 97 char = l;code = 108 char = ;code = 32 char = a;code = 97 char = c;code = 99 char = t;code = 116 char = i;code = 105 char = v;code = 118 char = i;code = 105 char = t;code = 116 char = y;code = 121 char = ,;code = 44 char = ;code = 32 char = 3;code = 51 char = -;code = 45 char = c;code = 99 char = y;code = 121 char = a;code = 97 char = n;code = 110 char = o;code = 111 char = -;code = 45 char = 2;code = 50 char = -;code = 45 char = (;code = 40 char = 4;code = 52 char = -;code = 45 char = n;code = 110 char = i;code = 105 char = t;code = 116 char = r;code = 114 char = o;code = 111 char = p;code = 112 char = h;code = 104 char = e;code = 101 char = n;code = 110 char = y;code = 121 char = l;code = 108 char = );code = 41 char = -;code = 45 char = 2;code = 50 char = H;code = 72 char = -;code = 45 char = i;code = 105 char = n;code = 110 char = d;code = 100 char = a;code = 97 char = z;code = 122 char = o;code = 111 char = l;code = 108 char = e;code = 101 char = ;code = 32 char = N;code = 78 char = 1;code = 49 char = -;code = 45 char = o;code = 111 char = x;code = 120 char = i;code = 105 char = d;code = 100 char = e;code = 101 char = ;code = 32 char = s;code = 115 char = h;code = 104 char = o;code = 111 char = w;code = 119 char = e;code = 101 char = d;code = 100 char = ;code = 32 char = l;code = 108 char = e;code = 101 char = i;code = 105 char = s;code = 115 char = h;code = 104 char = m;code = 109 char = a;code = 97 char = n;code = 110 char = o;code = 111 char = c;code = 99 char = i;code = 105 char = d;code = 100 char = a;code = 97 char = l;code = 108 char = ;code = 32 char = a;code = 97 char = c;code = 99 char = t;code = 116 char = i;code = 105 char = v;code = 118 char = i;code = 105 char = t;code = 116 char = y;code = 121 char = ;code = 32 char = i;code = 105 char = n;code = 110 char = ;code = 32 char = t;code = 116 char = h;code = 104 char = e;code = 101 char = ;code = 32 char = t;code = 116 char = h;code = 104 char = r;code = 114 char = e;code = 101 char = e;code = 101 char = ;code = 32 char = p;code = 112 char = a;code = 97 char = r;code = 114 char = a;code = 97 char = s;code = 115 char = i;code = 105 char = t;code = 116 char = i;code = 105 char = c;code = 99 char = ;code = 32 char = s;code = 115 char = t;code = 116 char = r;code = 114 char = a;code = 97 char = i;code = 105 char = n;code = 110 char = s;code = 115 char = ;code = 32 char = e;code = 101 char = v;code = 118 char = a;code = 97 char = l;code = 108 char = u;code = 117 char = a;code = 97 char = t;code = 116 char = e;code = 101 char = d;code = 100 char = .;code = 46 char = ;code = 32 char = T;code = 84 char = o;code = 111 char = ;code = 32 char = g;code = 103 char = a;code = 97 char = i;code = 105 char = n;code = 110 char = ;code = 32 char = i;code = 105 char = n;code = 110 char = s;code = 115 char = i;code = 105 char = g;code = 103 char = h;code = 104 char = t;code = 116 char = ;code = 32 char = i;code = 105 char = n;code = 110 char = t;code = 116 char = o;code = 111 char = ;code = 32 char = t;code = 116 char = h;code = 104 char = e;code = 101 char = ;code = 32 char = m;code = 109 char = e;code = 101 char = c;code = 99 char = h;code = 104 char = a;code = 97 char = n;code = 110 char = i;code = 105 char = s;code = 115 char = m;code = 109 char = ;code = 32 char = o;code = 111 char = f;code = 102 char = ;code = 32 char = a;code = 97 char = c;code = 99 char = t;code = 116 char = i;code = 105 char = o;code = 111 char = n;code = 110 char = ,;code = 44 char = ;code = 32 char = e;code = 101 char = l;code = 108 char = e;code = 101 char = c;code = 99 char = t;code = 116 char = r;code = 114 char = o;code = 111 char = c;code = 99 char = h;code = 104 char = e;code = 101 char = m;code = 109 char = i;code = 105 char = c;code = 99 char = a;code = 97 char = l;code = 108 char = ;code = 32 char = b;code = 98 char = e;code = 101 char = h;code = 104 char = a;code = 97 char = v;code = 118 char = i;code = 105 char = o;code = 111 char = u;code = 117 char = r;code = 114 char = ,;code = 44 char = ;code = 32 char = E;code = 69 char = S;code = 83 char = R;code = 82 char = ;code = 32 char = e;code = 101 char = x;code = 120 char = p;code = 112 char = e;code = 101 char = r;code = 114 char = i;code = 105 char = m;code = 109 char = e;code = 101 char = n;code = 110 char = t;code = 116 char = ,;code = 44 char = ;code = 32 char = i;code = 105 char = n;code = 110 char = h;code = 104 char = i;code = 105 char = b;code = 98 char = i;code = 105 char = t;code = 116 char = i;code = 105 char = o;code = 111 char = n;code = 110 char = ;code = 32 char = o;code = 111 char = f;code = 102 char = ;code = 32 char = p;code = 112 char = a;code = 97 char = r;code = 114 char = a;code = 97 char = s;code = 115 char = i;code = 105 char = t;code = 116 char = i;code = 105 char = c;code = 99 char = ;code = 32 char = r;code = 114 char = e;code = 101 char = s;code = 115 char = p;code = 112 char = i;code = 105 char = r;code = 114 char = a;code = 97 char = t;code = 116 char = i;code = 105 char = o;code = 111 char = n;code = 110 char = ;code = 32 char = a;code = 97 char = n;code = 110 char = d;code = 100 char = ;code = 32 char = Q;code = 81 char = S;code = 83 char = A;code = 65 char = R;code = 82 char = ;code = 32 char = w;code = 119 char = e;code = 101 char = r;code = 114 char = e;code = 101 char = ;code = 32 char = p;code = 112 char = e;code = 101 char = r;code = 114 char = f;code = 102 char = o;code = 111 char = r;code = 114 char = m;code = 109 char = e;code = 101 char = d;code = 100 char = .;code = 46 char = <;code = 60 char = b;code = 98 char = r;code = 114 char = /;code = 47 char = >;code = 62 result sql = A series of indazole N-oxide derivatives have been synthesized and their antichagasic and leishmanocidal properties studied. 3-Cyano-2-(4-iodophenyl)-2H-indazole N1-oxide exhibited interesting antichagasic activity on the two parasitic strains and the two parasitic stages evaluated. Furthermore, besides its trypanocidal activity, 3-cyano-2-(4-nitrophenyl)-2H-indazole N1-oxide showed leishmanocidal activity in the three parasitic strains evaluated. To gain insight into the mechanism of action, electrochemical behaviour, ESR experiment, inhibition of parasitic respiration and QSAR were performed.
Publication: Bioorg. Med. Chem. 2006 May 15 ;14(10)::3467-80.
Publication Date: 2006 May 15
Study Author(s): Gerpe, Alejandra;Aguirre, Gabriela;Boiani, Lucía;Cerecetto, Hugo;González, Mercedes;Olea-Azar, Claudio;Rigol, Carolina;Maya, Juan D;Morello, Antonio;Piro, Oscar E;Arán, Vicente J;Azqueta, Amaia;de Ceráin, Adela López;Monge, Antonio;Rojas, María Antonieta;Yaluff, Gloria;
Institution: Departamento de Química Orgánica, Facultad de Química-Facultad de Ciencias, Universidad de la República, Iguá 4225, Montevideo 11400, Uruguay.
Shortcut link to this study:
A series of indazole N-oxide derivatives have been synthesized and their antichagasic and leishmanocidal properties studied. 3-Cyano-2-(4-iodophenyl)-2H-indazole N1-oxide exhibited interesting antichagasic activity on the two parasitic strains and the two parasitic stages evaluated. Furthermore, besides its trypanocidal activity, 3-cyano-2-(4-nitrophenyl)-2H-indazole N1-oxide showed leishmanocidal activity in the three parasitic strains evaluated. To gain insight into the mechanism of action, electrochemical behaviour, ESR experiment, inhibition of parasitic respiration and QSAR were performed.
PMID: 16483783