Piperazine mono(dithio)carbamate ester compounds and analogs thereof: preparation method and uses thereof

A compound having the structure:

• 15
• wherein:
• is a divalent radical selected from CR1R2, O, S(O)0, 1, 2, NR3 or N+R3R4 X−;
• R1 is H, OH, NO2, COOH, CN, Cl, Br, I, keto (═O), thioketo (═S), imine (═NR, R is H, optionally substituted alkyl), an exocyclic double bond(═CH2), —SO3M or —OSO3M, wherein M is H, Na, K, Zn, Ca or meglumine, CSSH, COSH, CBr2, CF2, CF3, CCl2, CCl3, optionally substituted hydrocarbyl, optionally substituted alkoxy, optionally substituted alkylthio, amino, monoalkylamino, dialkylamino, optionally substituted alkylcarbonyl, optionally substituted alkoxycarbonyl, alkylcarbonyloxy, optionally substituted heteroaryl, optionally substituted aroyl, optionally substituted arylcarbonyl, optionally substituted aryloxycarbonyl, optionally substituted arylcarbonyloxy, aralkyloxy, optionally substituted heteroarylcarbonyl, optionally substituted arylthio, carbamoyl, monoalkylcarbamoyl, di-alkylcarbamoyl, arylcarbamoyl, optionally substituted organosulfinyl, optionally substituted organosulfonyl, aryloxy, optionally halogenated alkylsulfonylamino, optionally halogenated arylsulfonylamino, acyl, acyloxy, optionally substituted heterocyclic, a carbamate group, a sulfonamide group, sulfuryl, an amide group, or an optionally substituted ester group;
• R2 is absent when R1 is keto, thioketo, imine, or an exocyclic double bond, or R2 is H, OH, NO2, COOH, CN, Cl, Br, I, —SO3M or —OSO3M, wherein M is H, Na, K, Zn, Ca or meglumine;
• CSSH, COSH, CBr2, CF2, CF3, CCl2, CCl3, optionally substituted hydrocarbyl, optionally substituted alkoxy, optionally substituted alkylthio, amino, monoalkylamino, dialkylamino, optionally substituted alkylcarbonyl, optionally substituted alkoxycarbonyl, alkylcarbonyloxy, optionally substituted heteroaryl, optionally substituted aroyl, optionally substituted arylcarbonyl, optionally substituted aryloxycarbonyl, optionally substituted arylcarbonyloxy, aralkyloxy, optionally substituted heteroarylcarbonyl, optionally substituted arylthio, carbamoyl, monoalkylcarbamoyl, di-alkylcarbamoyl, arylcarbamoyl, optionally substituted organosulfinyl, optionally substituted organosulfonyl, aryloxy, optionally halogenated alkylsulfonylamino, optionally halogenated arylsulfonylamino, acyl, acyloxy, optionally substituted heterocyclic, a carbamate group, a sulfonamide group, sulfuryl, an amide group, or an optionally substituted ester group;
• R3 is H, optionally substituted hydrocarbyl, optionally substituted heteroaryl, optionally substituted aroyl, optionally substituted acyl, optionally substituted heterocyclic, hydroxyl, optionally substituted alkoxy, optionally substituted alkylthio, amino, optionally substituted alkylamino, optionally substituted dialkylamino, optionally substituted organosulfonyl, optionally substituted organosulfinyl, an optionally substituted alkylsulfonate ester group, optionally substituted alkylamino carbonyl, optionally substituted alkylamino thiocarbonyl, an optionally substituted alkyl ester group, an optionally substituted alkyl thioester group, an optionally substituted sulfonamide group, an optionally substituted alkyl carbonate group, an optionally substituted alkyl thiocarbonate group or an optionally substituted phosphonate group;
• R4 is optionally present when X− is present;
• when present, R4 is H, optionally substituted hydrocarbyl, optionally substituted heteroaryl or optionally substituted heterocyclic;
• R5 is optionally present, and when present each R5 is independently selected from OH, NO2, COOH, CN, Cl, Br, I, keto (═O), thioketo (═S), imine (═NR, R is H, optionally substituted alkyl), an exocyclic double bond(═CH2), —SO3M or —OSO3M, wherein M is H, Na, K, Zn, Ca or meglumine, CSSH, COSH, CBr2, CF2, CF3, CCl2, CCl3, optionally substituted hydrocarbyl, optionally substituted alkoxy, optionally substituted alkylthio, amino, monoalkylamino, dialkylamino, optionally substituted alkylcarbonyl, optionally substituted alkoxycarbonyl, alkylcarbonyloxy, optionally substituted heteroaryl, optionally substituted aroyl, optionally substituted arylcarbonyl, optionally substituted aryloxycarbonyl, optionally substituted arylcarbonyloxy, aralkyloxy, optionally substituted heteroarylcarbonyl, optionally substituted arylthio, carbamoyl, monoalkylcarbamoyl, di-alkylcarbamoyl, arylcarbamoyl, optionally substituted organosulfinyl, optionally substituted organosulfonyl, aryloxy, optionally halogenated alkylsulfonylamino, optionally halogenated arylsulfonylamino, acyl, acyloxy, optionally substituted heterocyclic, a carbamate group, a sulfonamide group, sulfuryl, an amide group, or an optionally substituted ester group;
• R6 is optionally substituted alkylene, hydrocarbylene, optionally substituted aminoalkylene, or optionally substituted heterocyclic;
• R7 is H, CN, COOH, OH, Br, Cl, I, optionally substituted aryl, optionally substituted heteroaryl, or R7 and Ar can cooperate to form a macrocycle;
• R8 is H, OH, NO2, COOH, tetrazolyl, C(O)NHOH, CN, Cl, Br, I, —SO3M, or OSO2M, wherein M is H, Na, K, Zn, Ca or meglumine, CSSH, COSH, CBr2, CF2, CF3, CCl2, CCl3, optionally substituted hydrocarbyl, optionally substituted alkoxy, optionally substituted alkylthio, amino, monoalkylamino, dialkylamino, optionally substituted alkylcarbonyl;
• optionally substituted alkoxycarbonyl;
• alkylcarbonyloxy;
• optionally substituted heteroaryl, optionally substituted aroyl, optionally substituted arylcarbonyl, optionally substituted aryloxycarbonyl, optionally substituted arylcarbonyloxy, aralkyloxy, optionally substituted heteroarylcarbonyl, optionally substituted arylthio, carbamoyl, monoalkylcarbamoyl, di-alkylcarbamoyl, arylcarbamoyl, optionally substituted organosulfinyl, optionally substituted organosulfonyl, aryloxy, optionally halogenated alkylsulfonylamino or arylsulfonylamino, acyl, acyloxy, optionally substituted heterocyclic, a carbamate group, a sulfonamide group, sulfuryl, COOR9, COONR10R11, wherein R9, R10 and R11 are independently selected from C1-10 alkyl;
• Ar is optionally substituted aryl, optionally substituted heteroaryl, or Ar and R7 can cooperate to form a macrocycle;
• X− is present only when R4 is present;
• and when X− is present, it is Cl−, Br−, I−, F− nitrate, phosphate, sulfate, acetate, adipate, besylate, camyslate, citrate, edisylate, estolate, fumarate, gluceptate, gluconate, glucuronate, hippurate, hyclate, lactate, lactobionate, maleate, napsylate, oleate, pamoate, stearate, succinate, sulfosalicylate, tannate, tartrate, terephthalate, tosylate, or triethiodide;
• m and n are independently integers from 0 up to 5;
• x is an integer from 0 up to 4;
• Y is a divalent radical selected from CR1R2, O or S;
• and
• Z is O or S.