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ANTIBIOTIC CC 1065
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Name

ANTIBIOTIC CC 1065

 EINECS N/A
CAS No. 69866-21-3 Density 1.75g/cm3
PSA 210.31000 LogP 4.62030
Solubility N/A Melting Point N/A
Formula C37H33 N7 O8 Boiling Point 704.36°C (rough estimate)
Molecular Weight 703.711 Flash Point N/A
Transport Information N/A Appearance N/A
Safety Deadly poison by intravenous and intraperitoneal routes. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx. Risk Codes N/A
Molecular Structure Molecular Structure of 69866-21-3 (Rachelmycin) Hazard Symbols N/A
Synonyms

Benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxamide,7-[[1,6-dihydro-4-hydroxy-5-methoxy-7-[(4,5,8,8a-tetrahydro-7-methyl-4-oxocyclopropa[c]benzo[1,2-b:4,3-b']dipyrrol-2(1H)-yl)carbonyl]benzo[1,2-b:4,3-b']dipyrrol-3(2H)-yl]carbonyl]-1,6-dihydro-4-hydroxy-5-methoxy-,(7bR)-; Benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxamide,7-[[1,6-dihydro-4-hydroxy-5-methoxy-7-[(4,5,8,8a-tetrahydro-7-methyl-4-oxocyclopropa[c]pyrrolo[3,2-e]indol-2(1H)-yl)carbonyl]benzo[1,2-b:4,3-b']dipyrrol-3(2H)-yl]carbonyl]-1,6-dihydro-4-hydroxy-5-methoxy-,(7bR,8aS)- (9CI); Cyclopropa[c]benzo[1,2-b:4,3-b']dipyrrole,benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxamide deriv.; (+)-CC 1065; Antibiotic CC1065; CC 1065; CC 1065, (+)-; MCMC 10279; NSC 298223; Rachelmycin

Article Data 5

ANTIBIOTIC CC 1065 Synthetic route

112764-71-3

C37H34ClN7O8

69866-21-3

CC-1065

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile for 4h; Ambient temperature;45%
With triethylamine In water; acetonitrile at 22℃; for 0.5h;43%
With triethylamine In water; acetonitrile at 23℃; for 0.5h; Yield given;
With triethylamine In water; acetonitrile for 1h; Ambient temperature; Yield given;
110314-51-7

tert-butyl-(1S)-1-(chloromethyl)-5-hydroxy-8-methyl-1,6-dihydropyrrolo[3,2-e]indole-3(2H)-carboxylate

69866-21-3

CC-1065

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 3M HCl / ethyl acetate / 1 h / Ambient temperature
2: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / Ambient temperature
3: 45 percent / DBU / acetonitrile / 4 h / Ambient temperature
View Scheme
Multi-step reaction with 3 steps
1: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C
2: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C
3: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C
View Scheme
Multi-step reaction with 3 steps
1: 3N HCl / ethyl acetate / 0.75 h / 23 °C
2: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C
3: Et3N / H2O; acetonitrile / 0.5 h / 23 °C
View Scheme
Multi-step reaction with 3 steps
1: hydrogen chloride gas / ethyl acetate / 0.67 h
2: 54 percent / EDC / N,N-dimethyl-acetamide / 2 h / Ambient temperature
3: triethylamine / acetonitrile; H2O / 1 h / Ambient temperature
View Scheme
112836-67-6

(S)-1,6-dihydro-1-(hydroxymethyl)-8-methyl-5-(phenylmethoxy)-benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxylic acid 1,1-dimethylethyl ester

69866-21-3

CC-1065

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 82 percent / PPh3, CCl4 / CH2Cl2 / 7 h / Ambient temperature
2: 88 percent / 25percent HCO2NH4 / 10percentPd-C / tetrahydrofuran / 6 h / 0 °C
3: 3M HCl / ethyl acetate / 1 h / Ambient temperature
4: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / Ambient temperature
5: 45 percent / DBU / acetonitrile / 4 h / Ambient temperature
View Scheme
Multi-step reaction with 5 steps
1: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C
2: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C
3: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C
4: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C
5: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C
View Scheme
Multi-step reaction with 5 steps
1: 87 percent / CCl4, Ph3P / CH2Cl2 / 12 h / 23 °C
2: 100 percent / aq. HCO2NH4 / 10percent Pd/C / tetrahydrofuran / 0.75 h / 23 °C
3: 3N HCl / ethyl acetate / 0.75 h / 23 °C
4: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C
5: Et3N / H2O; acetonitrile / 0.5 h / 23 °C
View Scheme
Multi-step reaction with 6 steps
1: pyridine / 6 h / Ambient temperature
2: lithium chloride / dimethylformamide / 0.42 h / 80 °C
3: ammonium formate / 10percent Pd/C / tetrahydrofuran; methanol / 0.33 h / Ambient temperature
4: hydrogen chloride gas / ethyl acetate / 0.67 h
5: 54 percent / EDC / N,N-dimethyl-acetamide / 2 h / Ambient temperature
6: triethylamine / acetonitrile; H2O / 1 h / Ambient temperature
View Scheme
110314-50-6

(S)-1-(chloromethyl)-1,6-dihydro-8-methyl-5-(phenylmethoxy)-benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxylic acid 1,1-dimethylethyl ester

69866-21-3

CC-1065

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 88 percent / 25percent HCO2NH4 / 10percentPd-C / tetrahydrofuran / 6 h / 0 °C
2: 3M HCl / ethyl acetate / 1 h / Ambient temperature
3: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / Ambient temperature
4: 45 percent / DBU / acetonitrile / 4 h / Ambient temperature
View Scheme
Multi-step reaction with 4 steps
1: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C
2: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C
3: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C
4: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C
View Scheme
Multi-step reaction with 4 steps
1: 100 percent / aq. HCO2NH4 / 10percent Pd/C / tetrahydrofuran / 0.75 h / 23 °C
2: 3N HCl / ethyl acetate / 0.75 h / 23 °C
3: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C
4: Et3N / H2O; acetonitrile / 0.5 h / 23 °C
View Scheme
Multi-step reaction with 4 steps
1: ammonium formate / 10percent Pd/C / tetrahydrofuran; methanol / 0.33 h / Ambient temperature
2: hydrogen chloride gas / ethyl acetate / 0.67 h
3: 54 percent / EDC / N,N-dimethyl-acetamide / 2 h / Ambient temperature
4: triethylamine / acetonitrile; H2O / 1 h / Ambient temperature
View Scheme
110314-54-0

(S)-1-(chloromethyl)-1,6-dihydro-5-hydroxy-8-methylbenzo[1,2-b:4,3-b']dipyrrole hydrochloride

69866-21-3

CC-1065

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / Ambient temperature
2: 45 percent / DBU / acetonitrile / 4 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C
2: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C
View Scheme
Multi-step reaction with 2 steps
1: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C
2: Et3N / H2O; acetonitrile / 0.5 h / 23 °C
View Scheme
Multi-step reaction with 2 steps
1: 54 percent / EDC / N,N-dimethyl-acetamide / 2 h / Ambient temperature
2: triethylamine / acetonitrile; H2O / 1 h / Ambient temperature
View Scheme

(3S)-3-acetoxymethyl-5-amino-6-benzyloxy-1-(t-butoxycarbonyl)-2,3-dihydroindole

69866-21-3

CC-1065

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 96 percent / methanol / 0 deg C - r.t., overnight
2: 23 percent / Pd(OAc)2 / N,N-dimethyl-acetamide / 70 °C
3: 48 percent / Me2SBH3 / tetrahydrofuran / 19 h / Heating
4: 82 percent / PPh3, CCl4 / CH2Cl2 / 7 h / Ambient temperature
5: 88 percent / 25percent HCO2NH4 / 10percentPd-C / tetrahydrofuran / 6 h / 0 °C
6: 3M HCl / ethyl acetate / 1 h / Ambient temperature
7: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / Ambient temperature
8: 45 percent / DBU / acetonitrile / 4 h / Ambient temperature
View Scheme
176685-39-5

(S)-8-Acetoxymethyl-4-benzyloxy-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1,6-dicarboxylic acid 6-tert-butyl ester 1-methyl ester

69866-21-3

CC-1065

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 48 percent / Me2SBH3 / tetrahydrofuran / 19 h / Heating
2: 82 percent / PPh3, CCl4 / CH2Cl2 / 7 h / Ambient temperature
3: 88 percent / 25percent HCO2NH4 / 10percentPd-C / tetrahydrofuran / 6 h / 0 °C
4: 3M HCl / ethyl acetate / 1 h / Ambient temperature
5: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / Ambient temperature
6: 45 percent / DBU / acetonitrile / 4 h / Ambient temperature
View Scheme
176685-38-4

(S)-3-Acetoxymethyl-6-benzyloxy-5-((E)-2-methoxycarbonyl-vinylamino)-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester

69866-21-3

CC-1065

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 23 percent / Pd(OAc)2 / N,N-dimethyl-acetamide / 70 °C
2: 48 percent / Me2SBH3 / tetrahydrofuran / 19 h / Heating
3: 82 percent / PPh3, CCl4 / CH2Cl2 / 7 h / Ambient temperature
4: 88 percent / 25percent HCO2NH4 / 10percentPd-C / tetrahydrofuran / 6 h / 0 °C
5: 3M HCl / ethyl acetate / 1 h / Ambient temperature
6: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / Ambient temperature
7: 45 percent / DBU / acetonitrile / 4 h / Ambient temperature
View Scheme
38880-89-6

N-(2-hydroxy-4-nitrophenyl)benzamide

69866-21-3

CC-1065

Conditions
ConditionsYield
Multi-step reaction with 18 steps
1: 94 percent / K2CO3 / n-Bu4NI / acetone / 16 h / Heating
2: 90 percent / Na2S2O4 / tetrahydrofuran; H2O / 30 h / Heating
3: pyridine / tetrahydrofuran / 18 h / 22 °C
4: 84 percent / lead tetraacetate / benzene / 8 h / 22 °C
5: CH2Cl2 / 10 h / 23 °C
6: 10percent aq. hydrochloric acid / tetrahydrofuran / 20 h / 23 °C
7: 99 percent / conc. sulfuric acid, N-bromosuccinimide / tetrahydrofuran / 1 h / -23 °C
8: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h
9: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating
10: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min
11: 83 percent / acetyl chloride / methanol / 2 h / 50 °C
12: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C
13: tetrahydrofuran / 20 h / 23 °C
14: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C
15: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C
16: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C
17: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C
18: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C
View Scheme
112764-62-2

N-[4-[(Z)-Benzenesulfonylimino]-2-benzyloxy-cyclohexa-2,5-dien-(Z)-ylidene]-benzamide

69866-21-3

CC-1065

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1: 2.) 10percent aq. HCl / 1.) CH2Cl2, 0 - 23 deg C, 12 h 2.) THF, 23 deg C, 12 h
2: 97 percent / N-bromosuccinimide / H2SO4 / tetrahydrofuran / 1 h / -23 °C
3: 1.) NaH / 1.) DMF, 23 deg C, 15 min 2.) DMF, 23 deg C, 3 h
4: n-Bu3SnH / AIBN / benzene / 5 h / 80 °C
5: 1.) BH3*SMe2 2.) 2N aq. NaOH, 30percent H2O2 / 1.) THF, 0 - 23 deg C, 1 - 3 h 2.) 45 deg C, 30 min
6: 83 percent / 5percent HCl / methanol / 2 h / 50 °C
7: sodium bis(2-methoxyethoxy)aluminium hydride / toluene / 3 h / 100 °C
8: tetrahydrofuran / 3 h / 23 °C
9: 87 percent / CCl4, Ph3P / CH2Cl2 / 12 h / 23 °C
10: 100 percent / aq. HCO2NH4 / 10percent Pd/C / tetrahydrofuran / 0.75 h / 23 °C
11: 3N HCl / ethyl acetate / 0.75 h / 23 °C
12: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C
13: Et3N / H2O; acetonitrile / 0.5 h / 23 °C
View Scheme

ANTIBIOTIC CC 1065 Chemical Properties

Product Name: Antibiotic CC 1065 (CAS NO.69866-21-3)


Molecular Formula: C37H33N7O8
Molecular Weight: 703.7g/mol
Mol File: 69866-21-3.mol
Density: 1.75 g/cm3
Surface Tension: 125.7 dyne/cm
XLogP3-AA: 2.4
H-Bond Donor: 6
H-Bond Acceptor: 8

ANTIBIOTIC CC 1065 Toxicity Data With Reference

1.    

dni-mus:leu 4 µg/L

     CNREA8    Cancer Research. 42 (1982),999.
2.    

oms-mus:leu 45 µg/L

     CNREA8    Cancer Research. 42 (1982),999.
3.    

dni-ham:ovr 150 ng/L

     CNREA8    Cancer Research. 42 (1982),3532.
4.    

oms-ham:ovr 5 µg/L

     CNREA8    Cancer Research. 42 (1982),3532.
5.    

dnd-mam:lym 7400 nmol/L

     CNREA8    Cancer Research. 42 (1982),999.
6.    

ipr-mus LD50:6900 ng/kg

     JANTAJ    Journal of Antibiotics. 37 (1984),63.
7.    

ivn-mus LD50:9 µg/kg

     JANTAJ    Journal of Antibiotics. 37 (1984),63.
8.    

ivn-rbt LDLo:1 µg/kg

     JANTAJ    Journal of Antibiotics. 37 (1984),63.

ANTIBIOTIC CC 1065 Safety Profile

Deadly poison by intravenous and intraperitoneal routes. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

ANTIBIOTIC CC 1065 Specification

 Antibiotic CC 1065 ,its CAS NO. is 69866-21-3,the synonyms is Rachelmycin ; CC 1065 ; CCRIS 2174 ; NSC 298223 ; Benzo(1,2-b:4,3-b')dipyrrole-3(2H)-carboxamide, 7-((1,6-dihydro-4-hydroxy-5-methoxy-7-((4,5,8,8a-tetrahydro-7-
methyl-4-oxocyclopropa(c)pyrrolo(3,2-e)indol-2(1H)-yl)carbonyl)benzo(1,2-b:4,3-b')dipyrrol-3(2H)-yl)carbonyl)-
1,6-dihydro-4-hydroxy-5-methoxy-, (7bR)- .

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