Products Categories
CAS No.: | 35846-53-8 |
---|---|
Name: | maitansine |
Article Data: | 3 |
Molecular Structure: | |
Formula: | C34H46 Cl N3 O10 |
Molecular Weight: | 692.206 |
Synonyms: | L-Alanine, N-acetyl-N-methyl-,11-chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.110,14.03,5]hexacosa-10,12,14(26),16,18-pentaen-6-ylester, [1S-(1R*,2S*,3R*,5R*,6R*,16E,18E,20S*,21R*)]-;Maitansine;Maysanine;Maytansin;N-Acetyl-N-methyl-L-alanine [1S-(1R*,2S*,3R*,5R*,6R*,16E,18E,20S*,21R*)]-11-chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.110,14.03,5]hexacosa-10,12,14(26),16,18-pentaen-6-ylester;NSC 153858; |
EINECS: | 252-754-7 |
Density: | 1.32g/cm3 |
Melting Point: | 183.5-184℃ |
Boiling Point: | 895.1°Cat760mmHg |
Flash Point: | 495.1°C |
Safety: | A deadly poison by intraperitoneal and intravenous routes. Moderately toxic by subcutaneous route. Human systemic effects by intravenous route: hallucinations, distorted perceptions, change in motor activity, and nausea or vomiting. An experimental teratogen. Mutation data reported. Used as an antineoplastic agent. When heated to decomposition it emits very toxic fumes of Cl− and NOx. |
PSA: | 156.47000 |
LogP: | 3.92820 |
maytansine 9-O-methyl ether
maytansine
Conditions | Yield |
---|---|
With pyridine hydrochloride In tetrahydrofuran at 25℃; for 14h; | 95% |
4-deoxymaytansinol
maytansine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 0.1 percent p-toluenesulfonic acid / 0.5 h / 25 °C 2: 87 percent / tert-butyl hydroperoxide, oxyvanadium(IV) bis(acetylacetonate), 2,6-lutidine / benzene; toluene / 3.5 h / 25 °C 3: imidazole / dimethylformamide; 1,2-dimethoxy-ethane / 75 h / 45 - 47 °C 4: 95 percent / aq. pyridinium chloride / tetrahydrofuran / 14 h / 25 °C View Scheme |
(3E,5E,14E)-(7R,8S,12S,13S,16S)-21-Chloro-16-hydroxy-7,8,22-trimethoxy-3,13,15,19-tetramethyl-11-oxa-9,19-diaza-tricyclo[18.3.1.18,12]pentacosa-1(24),3,5,14,20,22-hexaene-10,18-dione
maytansine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 87 percent / tert-butyl hydroperoxide, oxyvanadium(IV) bis(acetylacetonate), 2,6-lutidine / benzene; toluene / 3.5 h / 25 °C 2: imidazole / dimethylformamide; 1,2-dimethoxy-ethane / 75 h / 45 - 47 °C 3: 95 percent / aq. pyridinium chloride / tetrahydrofuran / 14 h / 25 °C View Scheme |
C36H56ClNO5S2Si
maytansine
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 1.) pyridine, 2.) aq. ammonium hydroxide / 1.) 27 deg C, 20 min, 2.) tert-butyl alcohol, 27 deg C, 2 h 2: mercuric chloride, aq. calcium carbonate / acetonitrile / 12 h / 25 °C 3: 83 percent / aq. HF / acetonitrile / 0.75 h / 0 °C 4: 0.1 percent p-toluenesulfonic acid / 0.5 h / 25 °C 5: 87 percent / tert-butyl hydroperoxide, oxyvanadium(IV) bis(acetylacetonate), 2,6-lutidine / benzene; toluene / 3.5 h / 25 °C 6: imidazole / dimethylformamide; 1,2-dimethoxy-ethane / 75 h / 45 - 47 °C 7: 95 percent / aq. pyridinium chloride / tetrahydrofuran / 14 h / 25 °C View Scheme |
3-O-(tert-butyldimethylsilyl)-4,5-deoxymaytansinol
maytansine
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 83 percent / aq. HF / acetonitrile / 0.75 h / 0 °C 2: 0.1 percent p-toluenesulfonic acid / 0.5 h / 25 °C 3: 87 percent / tert-butyl hydroperoxide, oxyvanadium(IV) bis(acetylacetonate), 2,6-lutidine / benzene; toluene / 3.5 h / 25 °C 4: imidazole / dimethylformamide; 1,2-dimethoxy-ethane / 75 h / 45 - 47 °C 5: 95 percent / aq. pyridinium chloride / tetrahydrofuran / 14 h / 25 °C View Scheme |
C37H57ClN2O6S2Si
maytansine
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: mercuric chloride, aq. calcium carbonate / acetonitrile / 12 h / 25 °C 2: 83 percent / aq. HF / acetonitrile / 0.75 h / 0 °C 3: 0.1 percent p-toluenesulfonic acid / 0.5 h / 25 °C 4: 87 percent / tert-butyl hydroperoxide, oxyvanadium(IV) bis(acetylacetonate), 2,6-lutidine / benzene; toluene / 3.5 h / 25 °C 5: imidazole / dimethylformamide; 1,2-dimethoxy-ethane / 75 h / 45 - 47 °C 6: 95 percent / aq. pyridinium chloride / tetrahydrofuran / 14 h / 25 °C View Scheme |
maytansine
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: 1.) 2-propanethiol, boron trifluoride etherate, 2.) silver nitrate, aq. 2,6-lutidine / 1.) methylene chloride, - 78 deg C, 5 min, 2.) THF, 25 deg C, 1.75 h 2: 1.) pyridine, 2.) aq. ammonium hydroxide / 1.) 27 deg C, 20 min, 2.) tert-butyl alcohol, 27 deg C, 2 h 3: mercuric chloride, aq. calcium carbonate / acetonitrile / 12 h / 25 °C 4: 83 percent / aq. HF / acetonitrile / 0.75 h / 0 °C 5: 0.1 percent p-toluenesulfonic acid / 0.5 h / 25 °C 6: 87 percent / tert-butyl hydroperoxide, oxyvanadium(IV) bis(acetylacetonate), 2,6-lutidine / benzene; toluene / 3.5 h / 25 °C 7: imidazole / dimethylformamide; 1,2-dimethoxy-ethane / 75 h / 45 - 47 °C 8: 95 percent / aq. pyridinium chloride / tetrahydrofuran / 14 h / 25 °C View Scheme |
maytansine
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1: 71 percent / mesitylenesulfonyl chloride, diisopropylethylamine / benzene / 28 h / 40 °C 2: 1.) 2-propanethiol, boron trifluoride etherate, 2.) silver nitrate, aq. 2,6-lutidine / 1.) methylene chloride, - 78 deg C, 5 min, 2.) THF, 25 deg C, 1.75 h 3: 1.) pyridine, 2.) aq. ammonium hydroxide / 1.) 27 deg C, 20 min, 2.) tert-butyl alcohol, 27 deg C, 2 h 4: mercuric chloride, aq. calcium carbonate / acetonitrile / 12 h / 25 °C 5: 83 percent / aq. HF / acetonitrile / 0.75 h / 0 °C 6: 0.1 percent p-toluenesulfonic acid / 0.5 h / 25 °C 7: 87 percent / tert-butyl hydroperoxide, oxyvanadium(IV) bis(acetylacetonate), 2,6-lutidine / benzene; toluene / 3.5 h / 25 °C 8: imidazole / dimethylformamide; 1,2-dimethoxy-ethane / 75 h / 45 - 47 °C 9: 95 percent / aq. pyridinium chloride / tetrahydrofuran / 14 h / 25 °C View Scheme |
(-)-maytansinol
maytansine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: imidazole / dimethylformamide; 1,2-dimethoxy-ethane / 75 h / 45 - 47 °C 2: 95 percent / aq. pyridinium chloride / tetrahydrofuran / 14 h / 25 °C View Scheme |
methanol
maytansine
(3E,5E,7R,84Ξ,86S)-12c-(N-acetyl-N-methyl-L-alanyloxy)-14-chloro-10t,11c-epoxy-15,7r,84-trimethoxy-3,9c,11t,15-tetramethyl-15-aza-1(1,3)-benzena-8(4,6)-[1,3]oxazinana-cyclopentadecaphane-3,5-diene-82,14-dione
Conditions | Yield |
---|---|
With trifluoroacetic acid In benzene Ambient temperature; |
Maytansine, with the CAS NO. 35846-53-8, is also called Maitansine; Maysanine; Maytansin. Maytansine is an ansamycin antibiotic originally isolated from the Ethiopian shrub Maytenus serrata. Maytansine binds to tubulin at the rhizoxin binding site, thereby inhibiting microtubule assembly, inducing microtubule disassembly, and disrupting mitosis.
Physical properties about Maytansine are: (1)ACD/LogP: 4.066; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): 4.07; (4)ACD/LogD (pH 7.4): 4.07; (5)ACD/BCF (pH 5.5): 724.76; (6)ACD/BCF (pH 7.4): 722.57; (7)ACD/KOC (pH 5.5): 3880.82; (8)ACD/KOC (pH 7.4): 3869.11; (9)#H bond acceptors: 13; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 7; (12)Index of Refraction: 1.59 ; (13)Molar Refractivity: 176.691 cm3; (14)Molar Volume: 523.775 cm3; (15)Polarizability: 70.046 10-24cm3; (16)Surface Tension: 57.5769996643066 dyne/cm; (17)Density: 1.322 g/cm3; (18)Flash Point: 495.133 °C; (19)Enthalpy of Vaporization: 136.306 kJ/mol; (20)Boiling Point: 895.091 °C at 760 mmHg
You can still convert the following datas into molecular structure:
(1)InChI=1S/C34H46ClN3O10/c1-18-11-10-12-26(45-9)34(43)17-25(46-32(42)36-34)19(2)30-33(5,48-30)27(47-31(41)20(3)37(6)21(4)39)16-28(40)38(7)23-14-22(13-18)15-24(44-8)29(23)35/h10-12,14-15,19-20,25-27,30,43H,13,16-17H2,1-9H3,(H,36,42)/b12-10-,18-11+/t19-,20+,25+,26-,27-,30-,33+,34+/m1/s1;
(2)InChIKey=WKPWGQKGSOKKOO-AQPVFDFWSA-N;
(3)SmilesC[C@@H]1[C@@H]2C[C@]([C@@H](/C=C\C=C(\Cc3cc(c(c(c3)OC)Cl)N(C(=O)C[C@H]([C@]4([C@@H]1O4)C)OC(=O)[C@H](C)N(C)C(=O)C)C)/C)OC)(NC(=O)O2)O;
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
human | TDLo | intravenous | 190ug/kg/5D (.19mg/kg) | GASTROINTESTINAL: NAUSEA OR VOMITING BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) | Journal of the National Cancer Institute. Vol. 60, Pg. 93, 1978. |
mouse | LD50 | intraperitoneal | 245ug/kg (.245mg/kg) | National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986, | |
mouse | LD50 | intravenous | 1530ug/kg (1.53mg/kg) | BLOOD: THROMBOCYTOPENIA BLOOD: LEUKOPENIA SKIN AND APPENDAGES (SKIN): HAIR: OTHER | National Technical Information Service. Vol. PB82-165507, |
rat | LD50 | subcutaneous | 480ug/kg (.48mg/kg) | Cancer Treatment Reports. Vol. 61, Pg. 1333, 1977. | |
rat | LD50 | subcutaneous | 480ug/kg (.48mg/kg) | LUNGS, THORAX, OR RESPIRATION: DYSPNEA GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" | Cancer Treatment Reports. Vol. 61, Pg. 1333, 1977. |