91421-43-1 Usage
Uses
9-Amino Camptothecin is a derivative of Camptothecin (C175150), as antitumor agent.
Biological Activity
9-amino camptothecin is a topoisomerase i inhibitor [1][2].dna topoisomerases relax dna torsional strain generated during replication, transcription, recombination, repair, and chromosome condensation. the relaxation of dna supercoiling by topoisomerase i is enabled by a mechanism of controlled rotation around a transient dna single-strand break. camptothecin (cpt) is isolated from the bark of the chinese tree camptotheca accuminata [3].9-amino camptothecin, a water-soluble camptothecin analogue, is a topoisomerase i inhibitor. in human ht-29 colon adenocarcinoma, 9-amino camptothecin (9-ac) exhibited cytotoxicity with ic50 value of 19 nm. 9-ac also induced dna damage in whole cells and nuclei at a concenstration of 85 nm and 21 nm, respectively [1].9-amino camptothecin had greater activity than camptothecin against human tumour xenografts, including lewis lung carcinoma and b16 melanoma. 9-ac had entered phase ii trials. in patients with advanced solid tumours, 9-amino camptothecin exhibited anti-tumor activity [1][2].
references
[1]. rothenberg, m.l. topoisomerase i inhibitors: review and update. annals of oncology 8(9), 837-855 (1997).[2]. dancey j, eisenhauer ea. current perspectives on camptothecins in cancer treatment. br j cancer. 1996 aug;74(3):327-38.[3]. drwal mn1, agama k, wakelin lp, et al. exploring dna topoisomerase i ligand space in search of novel anticancer agents. plos one. 2011;6(9):e25150.
Check Digit Verification of cas no
The CAS Registry Mumber 91421-43-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 9,1,4,2 and 1 respectively; the second part has 2 digits, 4 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 91421-43:
(7*9)+(6*1)+(5*4)+(4*2)+(3*1)+(2*4)+(1*3)=111
111 % 10 = 1
So 91421-43-1 is a valid CAS Registry Number.
InChI:InChI=1/C20H17N3O4/c1-2-20(26)13-7-16-17-10(6-11-14(21)4-3-5-15(11)22-17)8-23(16)18(24)12(13)9-27-19(20)25/h3-7,26H,2,8-9,21H2,1H3/t20-/m0/s1
91421-43-1Relevant articles and documents
A practical regiospecific synthesis of 9-nitrocamptothecin
Fu, Qingquan,Chen, Zhiyong
, p. 1940 - 1942 (2007/10/03)
9-Nitrocamptothecin has shown potent antitumor activity against many types of human cancers. A practical scale-up procedure for this compound is reported by selective reduction of corresponding sulfonate. Georg Thieme Verlag Stuttgart.
Radiosynthesis of carbon-11-labeled camptothecin derivatives as potential positron emission tomography tracers for imaging of topoisomerase I in cancers
Gao, Mingzhang,Miller, Kathy D.,Sledge, George W.,Zheng, Qi-Huang
, p. 3865 - 3869 (2007/10/03)
Four carbon-11-labeled camptothecin derivatives, 9-[11C]methoxy- 20(S)-camptothecin ([11C]5), 10-[11C]methoxy-20(S)- camptothecin ([11C]7), 9-nitro-10-[11C]methoxy-20(S)- camptothecin ([11C]9), and 9-[([11C]trimethylamino)methyl] -10-hydroxy-20(S)-camptothecin ([11C]11), have been synthesized as potential positron emission tomography tracers for imaging of topoisomerase I in cancers.
Process for the preparation of 9-amino camptothecin
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, (2008/06/13)
9-Amino-20(S)-camptothecin (I) is prepared by reducing 12-nitro-20(S)-camptothecin (II); converting the resulting 12-amino-20(S)-camptothecin (III) into a compound of formula (IV) wherein X is a group which can be reductively removed; reacting the compound of formula (IV) with a nitrating agent, to obtain thereby the corresponding 9-nitro-20(S)-camptothecin compound of formula (V) substituted at the 12-position by the group X; reducing in a single step the compound of formula (V), so obtaining the 9-amino-20(S)-camptothecin of formula (I); or reducing the compound of formula (V), so obtaining the corresponding 9-amino-20(S)-camptothecin compound of formula (VI) substituted at the 12-position by the group X and reductively removing the X group from the compound of formula (VI), so obtaining 9-amino-20(S)-camptothecin.
