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6576-51-8

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Basic Information
CAS No.: 6576-51-8
Name: distamycin A hydrochloride from*streptomyces dist
Article Data: 3
Molecular Structure:
Molecular Structure of 6576-51-8 (distamycin A hydrochloride from*streptomyces dist)
Formula: C22H27 N9 O4 . Cl H
Molecular Weight: 517.975
Synonyms: 1H-Pyrrole-2-carboxamide,N-[5-[[(3-amino-3-iminopropyl)amino]carbonyl]-1-methyl-1H-pyrrol-3-yl]-4-[[[4-(formylamino)-1-methyl-1H-pyrrol-2-yl]carbonyl]amino]-1-methyl-,monohydrochloride (9CI); N,4':N',4''-Ter[pyrrole-2-carboxamide],N''-(2-amidinoethyl)-4-formamido-1,1',1''-trimethyl-, hydrochloride (7CI);N,4':N',4''-Ter[pyrrole-2-carboxamide],N''-(2-amidinoethyl)-4-formamido-1,1',1''-trimethyl-, monohydrochloride (8CI);Distamycin A hydrochloride; Distamycin hydrochloride; MEN 10399; Stallimycinhydrochloride
EINECS: 229-505-6
Melting Point: 184-187° (Arcamone, 1967). Also reported as 189-193° from ethanol-ethyl acetate (Bialer)
Boiling Point: 715.4 °C at 760 mmHg
Flash Point: 386.4 °C
Solubility: CLEAR YELLOW TO GREEN SOLUTION AT 20MG/ML IN ETHANOL
Appearance: YELLOW TO YELLOW WITH A BROWN CAST POWDER
Hazard Symbols: IrritantXi
Risk Codes: 43
Safety: Poison by intraperitoneal and intravenous routes. Mutation data reported. When heated to decomposition it emits very toxic fumes of NOx and HCl.
PSA: 181.06000
LogP: 3.67870
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77727-43-6

N-Succinimidyl 4-<<<4-<<<4-(Formylamino)-1-methylpyrrol-2-yl>carbonyl>amino>-1-methylpyrrol-2-yl>carbonyl>amino>-1-methylpyrrole-2-carboxylate

77152-88-6

(1-amino-3-ammoniopropylidene)ammonium dihydrobromide

6576-51-8

distamycin A hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; sodium hydrogencarbonate In 1,4-dioxane; water 1.) 15 min, ice-cooled, 2.) room temperature, overnight; Yield given;
3786-88-7

1-methyl-4-<1-methyl-4-(1-methyl-4-aminopyrrole-2-carboxamido)pyrrole-2-carboxamido>pyrrole-2-carboxamidopropionamidine hydrochloride

3197-61-3

N-formylimidazole

6576-51-8

distamycin A hydrochloride

Conditions
ConditionsYield
In tetrahydrofuran; methanol at -40℃; for 0.5h; Yield given;
6973-60-0

1-Methyl-2-pyrrolecarboxylic acid

6576-51-8

distamycin A hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 43 percent / 1.) 70percent nitric acid, acetic anhydride / 1.) a) -15 deg C, 0.5 h, b) RT, 20 min
2: SOCl2 / tetrahydrofuran / 0.08 h / Heating
3: Hunig's base / tetrahydrofuran / -20 - 20 °C
4: 1.) H2, 2.) HCl / 10percent Pd/C / 1.) methanol, 40 deg C, 1 atm, 2.) isopropanol, -30 deg C
5: 64 percent / 1,8-bis(dimethylamino)naphthalene, dicyclohexylcarbodiimide / tetrahydrofuran; dimethylformamide / 3 h / Ambient temperature
6: 1.) HCl, 2.) NH3 / 1.) EtOH, RT, 1.5 h, 2.) EtOH, 1 h, RT
7: 70 percent / H2 / 10percent Pd/C / methanol / 40 °C
8: methanol; tetrahydrofuran / 0.5 h / -40 °C
View Scheme
Multi-step reaction with 8 steps
1: 43 percent / 1.) 70percent nitric acid, acetic anhydride / 1.) a) -15 deg C, 0.5 h, b) RT, 20 min
2: SOCl2 / tetrahydrofuran / 0.08 h / Heating
3: 1.) H2, 2.) Hunig's base / 10percent Pd/C / 1.) MeOH, 1 atm, 2.) THF, 3) THF, RT, 30 min
4: 95 percent / NaOH / H2O; ethanol / Heating
5: 64 percent / 1,8-bis(dimethylamino)naphthalene, dicyclohexylcarbodiimide / tetrahydrofuran; dimethylformamide / 3 h / Ambient temperature
6: 1.) HCl, 2.) NH3 / 1.) EtOH, RT, 1.5 h, 2.) EtOH, 1 h, RT
7: 70 percent / H2 / 10percent Pd/C / methanol / 40 °C
8: methanol; tetrahydrofuran / 0.5 h / -40 °C
View Scheme
13138-78-8

1-methyl-4-nitro-pyrrol-2-carboxylic acid

6576-51-8

distamycin A hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: SOCl2 / tetrahydrofuran / 0.08 h / Heating
2: Hunig's base / tetrahydrofuran / -20 - 20 °C
3: 1.) H2, 2.) HCl / 10percent Pd/C / 1.) methanol, 40 deg C, 1 atm, 2.) isopropanol, -30 deg C
4: 64 percent / 1,8-bis(dimethylamino)naphthalene, dicyclohexylcarbodiimide / tetrahydrofuran; dimethylformamide / 3 h / Ambient temperature
5: 1.) HCl, 2.) NH3 / 1.) EtOH, RT, 1.5 h, 2.) EtOH, 1 h, RT
6: 70 percent / H2 / 10percent Pd/C / methanol / 40 °C
7: methanol; tetrahydrofuran / 0.5 h / -40 °C
View Scheme
Multi-step reaction with 7 steps
1: SOCl2 / tetrahydrofuran / 0.08 h / Heating
2: 1.) H2, 2.) Hunig's base / 10percent Pd/C / 1.) MeOH, 1 atm, 2.) THF, 3) THF, RT, 30 min
3: 95 percent / NaOH / H2O; ethanol / Heating
4: 64 percent / 1,8-bis(dimethylamino)naphthalene, dicyclohexylcarbodiimide / tetrahydrofuran; dimethylformamide / 3 h / Ambient temperature
5: 1.) HCl, 2.) NH3 / 1.) EtOH, RT, 1.5 h, 2.) EtOH, 1 h, RT
6: 70 percent / H2 / 10percent Pd/C / methanol / 40 °C
7: methanol; tetrahydrofuran / 0.5 h / -40 °C
View Scheme
Multi-step reaction with 8 steps
1: H2, 1.0 M Na2CO3(aq.) / 5percent Pd/C / 3.5 h / 3102.9 Torr / Ambient temperature
2: tetrahydrofuran; diethyl ether / 1.) 1 h, ice cooled, 2.) 2 h, ambient temperature
3: 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride / dimethylformamide / 40 °C
4: TFA / CH2Cl2
5: EDC / dimethylformamide / 40 °C
6: H2 / 5percent Pd/C / dimethylformamide / 2 h / 3102.9 Torr / Ambient temperature
7: 88 percent / DCC / dimethylformamide / 1.) 70 min, 0 deg C, 2.) 40 deg C, overnight
8: 1.) NaHCO3, 2.) HCl / H2O; dioxane / 1.) 15 min, ice-cooled, 2.) room temperature, overnight
View Scheme
97950-76-0

1-methyl-4-(1-methyl-4-nitropyrrole-2-carboxamido)pyrrole-2-carboxylic acid

6576-51-8

distamycin A hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 64 percent / 1,8-bis(dimethylamino)naphthalene, dicyclohexylcarbodiimide / tetrahydrofuran; dimethylformamide / 3 h / Ambient temperature
2: 1.) HCl, 2.) NH3 / 1.) EtOH, RT, 1.5 h, 2.) EtOH, 1 h, RT
3: 70 percent / H2 / 10percent Pd/C / methanol / 40 °C
4: methanol; tetrahydrofuran / 0.5 h / -40 °C
View Scheme
69910-20-9

methyl 1-methyl-4-(1-methyl-4-nitropyrrole-2-carboxamido)pyrrole-2-carbonate

6576-51-8

distamycin A hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 95 percent / NaOH / H2O; ethanol / Heating
2: 64 percent / 1,8-bis(dimethylamino)naphthalene, dicyclohexylcarbodiimide / tetrahydrofuran; dimethylformamide / 3 h / Ambient temperature
3: 1.) HCl, 2.) NH3 / 1.) EtOH, RT, 1.5 h, 2.) EtOH, 1 h, RT
4: 70 percent / H2 / 10percent Pd/C / methanol / 40 °C
5: methanol; tetrahydrofuran / 0.5 h / -40 °C
View Scheme
28494-51-1

1-methyl-4-nitro-1H-pyrrole-2-carbonyl chloride

6576-51-8

distamycin A hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: Hunig's base / tetrahydrofuran / -20 - 20 °C
2: 1.) H2, 2.) HCl / 10percent Pd/C / 1.) methanol, 40 deg C, 1 atm, 2.) isopropanol, -30 deg C
3: 64 percent / 1,8-bis(dimethylamino)naphthalene, dicyclohexylcarbodiimide / tetrahydrofuran; dimethylformamide / 3 h / Ambient temperature
4: 1.) HCl, 2.) NH3 / 1.) EtOH, RT, 1.5 h, 2.) EtOH, 1 h, RT
5: 70 percent / H2 / 10percent Pd/C / methanol / 40 °C
6: methanol; tetrahydrofuran / 0.5 h / -40 °C
View Scheme
Multi-step reaction with 6 steps
1: 1.) H2, 2.) Hunig's base / 10percent Pd/C / 1.) MeOH, 1 atm, 2.) THF, 3) THF, RT, 30 min
2: 95 percent / NaOH / H2O; ethanol / Heating
3: 64 percent / 1,8-bis(dimethylamino)naphthalene, dicyclohexylcarbodiimide / tetrahydrofuran; dimethylformamide / 3 h / Ambient temperature
4: 1.) HCl, 2.) NH3 / 1.) EtOH, RT, 1.5 h, 2.) EtOH, 1 h, RT
5: 70 percent / H2 / 10percent Pd/C / methanol / 40 °C
6: methanol; tetrahydrofuran / 0.5 h / -40 °C
View Scheme
13138-76-6

1-methyl-4-nitropyrrole-2-carboxylic acid methyl ester

6576-51-8

distamycin A hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 92 percent / aq. NaOH / Heating
2: SOCl2 / tetrahydrofuran / 0.08 h / Heating
3: Hunig's base / tetrahydrofuran / -20 - 20 °C
4: 1.) H2, 2.) HCl / 10percent Pd/C / 1.) methanol, 40 deg C, 1 atm, 2.) isopropanol, -30 deg C
5: 64 percent / 1,8-bis(dimethylamino)naphthalene, dicyclohexylcarbodiimide / tetrahydrofuran; dimethylformamide / 3 h / Ambient temperature
6: 1.) HCl, 2.) NH3 / 1.) EtOH, RT, 1.5 h, 2.) EtOH, 1 h, RT
7: 70 percent / H2 / 10percent Pd/C / methanol / 40 °C
8: methanol; tetrahydrofuran / 0.5 h / -40 °C
View Scheme
Multi-step reaction with 8 steps
1: 92 percent / aq. NaOH / Heating
2: SOCl2 / tetrahydrofuran / 0.08 h / Heating
3: 1.) H2, 2.) Hunig's base / 10percent Pd/C / 1.) MeOH, 1 atm, 2.) THF, 3) THF, RT, 30 min
4: 95 percent / NaOH / H2O; ethanol / Heating
5: 64 percent / 1,8-bis(dimethylamino)naphthalene, dicyclohexylcarbodiimide / tetrahydrofuran; dimethylformamide / 3 h / Ambient temperature
6: 1.) HCl, 2.) NH3 / 1.) EtOH, RT, 1.5 h, 2.) EtOH, 1 h, RT
7: 70 percent / H2 / 10percent Pd/C / methanol / 40 °C
8: methanol; tetrahydrofuran / 0.5 h / -40 °C
View Scheme
3185-95-3

1-methyl-4-nitro-1H-pyrrole-2-carboxylic acid (2-cyanoethyl)amide

6576-51-8

distamycin A hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 1.) H2, 2.) HCl / 10percent Pd/C / 1.) methanol, 40 deg C, 1 atm, 2.) isopropanol, -30 deg C
2: 64 percent / 1,8-bis(dimethylamino)naphthalene, dicyclohexylcarbodiimide / tetrahydrofuran; dimethylformamide / 3 h / Ambient temperature
3: 1.) HCl, 2.) NH3 / 1.) EtOH, RT, 1.5 h, 2.) EtOH, 1 h, RT
4: 70 percent / H2 / 10percent Pd/C / methanol / 40 °C
5: methanol; tetrahydrofuran / 0.5 h / -40 °C
View Scheme
2522-28-3

3-<1-methyl-4-<1-methyl-4-(1-methyl-4-nitropyrrole-2-carboxamido)pyrrole-2-carboxamido>pyrrole-2-carboxamido>propionitrile

6576-51-8

distamycin A hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) HCl, 2.) NH3 / 1.) EtOH, RT, 1.5 h, 2.) EtOH, 1 h, RT
2: 70 percent / H2 / 10percent Pd/C / methanol / 40 °C
3: methanol; tetrahydrofuran / 0.5 h / -40 °C
View Scheme
Raw Materials
3197-61-3
77152-88-6
13138-78-8
3185-95-3
77716-11-1
77716-21-3
6973-60-0
28494-51-1
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Chemistry

MF: C22H27N9O4. HCl
MW: 517.97
EINECS: 229-505-6
Following is the molecular structure of DISTAMYCIN A HYDROCHLORIDE:

Toxicity Data With Reference

1.   

dni-mus:lym 1900 nmol/L

   CBINA8    Chemico-Biological Interactions. 8 (1974),183.
2.   

oms-mus:lym 3200 nmol/L

   CBINA8    Chemico-Biological Interactions. 8 (1974),183.
3.   

dnd-mam:lym 200 µmol/

   EJBCAI    European Journal of Biochemistry. 26 (1972),81.
4.   

ipr-rat LD50:169 mg/kg

   MDACAP    Medicamentos de Actualidad. 13 (1977),319.
5.   

ipr-mus LD50:160 mg/kg

   MDACAP    Medicamentos de Actualidad. 13 (1977),319.
6.   

ivn-mus LD50:75 mg/kg

   MEIEDD    Merck Index. 11 (1989),1383.

RTECS  :WZ7110000

Safety Profile

Poison by intraperitoneal and intravenous routes. Mutation data reported. When heated to decomposition it emits very toxic fumes of NOx and HCl.

Hazard Codes : Xi (Irritant)
Risk Statements:  43 (May cause sensitization by skin contact)
Safety Statements : 36/37 (Wear suitable protective clothing and gloves)
WGK Germany:  3

Specification

storage temp:?20°C