[2-[[3-[(2-aminoethyl)methylamino]propyl]methylamino]ethyl]carbamic acid tert-butyl ester | 854190-22-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [2-[[3-[(2-aminoethyl)methylamino]propyl]methylamino]ethyl]carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[2-[3-[2-aminoethyl(methyl)amino]propyl-methylamino]ethyl]carbamate
• CAS: 854190-22-0
• 化学式: C₁₄H₃₂N₄O₂
• 分子量: 288.434
• InChiKey: LIAZLRMAWISEFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  20
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  70.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [2-[[3-[(2-aminoethyl)methylamino]propyl]methylamino]ethyl]carbamic acid tert-butyl ester 、 10H-indolo[3,2-b]quinoline-11-carboxylic acid 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以62%的产率得到[2-[[3-[[2-[(10H-indolo[3,2-b]quinoline-11-carbonyl)-amino]ethyl]methylamino]propyl]methyl-amino]ethyl]carbamic acid tert-butyl ester
  参考文献：
  名称：

  [EN] SUBSTITUTED QUINOLINES FOR THE TREATMENT OF CANCER
  [FR] QUINOLINES SUBSTITUES DESTINES AU TRAITEMENT DU CANCER

  摘要：

  式为G1-L-G2的化合物，其中-G1是结构与cryptolepine接近的基团，-L-是选择自(CH2)rNR''(CH2)s和-(CH2)rNR''(CH2)SNR''(CH2)t的单共价键或共价连接双基团，-R''和-R''是基团，相同或不同，选择自H和(C1-C3)-烷基；r，s和t是1到3之间的整数，-G2是H或结构与-G1接近的基团，是插入剂。它们是插入到DNA碱基对之间的化合物，并且可用作对抗癌症的治疗剂，通过对人类白血病细胞Jurkat E6-1和人类癌细胞GLC-4的体外细胞毒性测试进行评估。优选化合物是那些其中-G1通过一个羰基氨基与-L-结合，-L-是-(CH2)3NCH3(CH2)3或-(CH2)2NCH3(CH2)SNCH3(CH2)2-，其中s = 2或3。-G1是从(IIa)和(IIb)中选择的基团；-G2是从H、式为(IIa)的基团、式为(IIb)的基团、1,8-萘酰亚胺的N-基团、2-苯基喹啉的C4-基团和吖啶的C9-基团中选择的基团。

  公开号：

  WO2005054236A1

文献信息

• Substituted quinolines for the treatment of cancer
  申请人：Aymami Bofarull Juan

  公开号：US20070105784A1

  公开（公告）日：2007-05-10

  Compounds of formula G 1 -L-G 2 , where -G 1 is a radical structurally close to cryptolepine, -L- is a single covalent bond or a covalent linking biradical selected from (CH 2 ) r NR′″(CH 2 ) s and —(CH 2 ) r NR′″(CH 2 ) S NR″″(CH 2 ) t —, —R′″ and —R″″ are radicals, same or different, selected from the group consisting of H and (C 1 -C 3 )-alkyl; r , s and t are an integer from 1 to 3 and, -G 2 is H or a radical structurally close to -G 1 , are intercalators. They are compounds which intercalate between DNA base pairs, and are useful as therapeutic agents against cancer, as assess by an in vitro test of cytotoxicity with human leukemia cells Jurkat E6-1 and human carcinoma cells GLC-4. Preferred compounds are those where -G 1 is bonded to -L- through a carbonyl amino and -L- is —(CH 2 ) 3 NCH 3 (CH 2 ) 3 or —(CH 2 ) 2 NCH 3 (CH 2 ) S NCH 3 (CH 2 ) 2 — where s =2 or 3. -G 1 is a radical selected from (IIa) y (IIb); -G 2 is a radical selected from H, a radical of formula (IIa), a radical of formula (IIb), the N-radical of 1,8-naphthalimide, the C4-radical of 2-phenylquinoline, and the C9-radical of acridine.

  化合物的公式为G1-L-G2，其中-G1是结构上接近cryptolepine的基团，-L-是单一共价键或共价连接的双基团，选择自(CH2)rNR′″(CH2)s和—(CH2)rNR′″(CH2)SNR″″(CH2)t—，其中，-R′″和-R″″是基团，相同或不同，选择自H和(C1-C3)-烷基；r、s和t为1到3的整数；-G2是H或结构上接近于-G1的基团，是插入剂。它们是插入到DNA碱基对之间的化合物，并且可用作治疗癌症的治疗剂，通过对人类白血病细胞Jurkat E6-1和人类癌细胞GLC-4的细胞毒性的体外测试进行评估。首选化合物是通过羰基氨基与-L-相连的-G1，其中-L-是—(CH2)3NCH3(CH2)3或—(CH2)2NCH3(CH2)SNCH3(CH2)2—，其中s=2或3。-G1是从(IIa)和(IIb)中选择的基团；-G2是从H、公式(IIa)的基团、公式(IIb)的基团、1,8-萘酰亚胺的N-基团、2-苯基喹啉的C4-基团和吖啶的C9-基团中选择的基团。
• Substituted Quinolines for the Treatment of Cancer
  申请人：Aymami Bofarull Juan

  公开号：US20100331355A1

  公开（公告）日：2010-12-30

  Compounds of formula G 1 -L-G 2 , where G 1 , is a radical structurally close to cryptolepine, -L- is a single covalent bond or a covalent linking biradical selected from —(CH 2 ) r NR′″(CH 2 ) s — and —(CH 2 ) r NR′″(CH 2 ) s NR″″(CH 2 ) t —, —R′″ and —R″″ are radicals, same or different, selected from the group consisting of H and (C 1 -C 3 )-alkyl; r, s and t are an integer from 1 to 3 and -G 2 is H or a radical structurally close to -G 1 , are intercalators. They are compounds which intercalate between DNA base pairs, and are useful as therapeutic agents against cancer, as assess by an in vitro test of citotoxicity with human leukemia cells Jurkat E6-1 and human carcinoma cells GLC-4. Preferred compounds are those where -G 1 is bonded to -L- through a carbonyl amino and -L- is —(CH 2 ) 3 NCH 3 (CH 2 ) 3 — or —(CH 2 ) 2 NCH 3 (CH 2 ) s NCH 3 (CH 2 ) 2 — where s=2 or 3. -G 1 is a radical selected from (IIa) and (IIb); -G 2 is a radical selected from H, a radical of formula (IIa), a radical of formula (IIb), the N-radical of 1,8-naphthalimide, the C4-radical of 2-phenylquinoline and the C9-radical of acridine.

  式为G1-L-G2的化合物，其中G1是结构与cryptolepine相似的基团，-L-是单个共价键或从—（CH2）rNR′″（CH2）s—和—（CH2）rNR′″（CH2）sNR″″（CH2）t—中选择的共价键连接双基团，其中—R′″和—R″″是从H和（C1-C3）-烷基中选择的相同或不同的基团；r、s和t是从1到3的整数，-G2是H或结构与-G1相似的基团，它们是插入剂化合物。它们是插入到DNA碱基对之间的化合物，并可用作治疗癌症的药物，如通过对人类白血病细胞Jurkat E6-1和人类癌细胞GLC-4进行细胞毒性的体外测试所确定的。首选化合物是-G1通过一个羰基氨基与-L-连接，并且-L-是—（CH2）3NCH3（CH2）3—或—（CH2）2NCH3（CH2）sNCH3（CH2）2—其中s=2或3。-G1是从（IIa）和（IIb）中选择的基团；-G2是从H、公式（IIa）的基团、公式（IIb）的基团、1,8-萘酰亚胺的N基团、2-苯基喹啉的C4基团和吖啶的C9基团中选择的基团。
• SUBSTITUTED QUINOLINES FOR THE TREATMENT OF CANCER
  申请人：Crystax Pharmaceuticals S.L.

  公开号：EP1687304A1

  公开（公告）日：2006-08-09
• US7728000B2
  申请人：——

  公开号：US7728000B2

  公开（公告）日：2010-06-01
• [EN] SUBSTITUTED QUINOLINES FOR THE TREATMENT OF CANCER<br/>[FR] QUINOLINES SUBSTITUES DESTINES AU TRAITEMENT DU CANCER
  申请人：CRYSTAX PHARMACEUTICALS S L

  公开号：WO2005054236A1

  公开（公告）日：2005-06-16

  Compounds of formula G1-L-G2, where -G1 is a radical structurally close to cryptolepine, -L- is a single covalent bond or a covalent linking biradical selected from (CH2)rNR''(CH2)s and -(CH2)rNR''(CH2)SNR''(CH2)t -, -R'' and -R'' are radicals, same or different, selected from the group consisting of H and (C1-C3)-alkyl; r , s and t are an integer from 1 to 3 and, -G2 is H or a radical structurally close to -G1, are intercalators. They are compounds which intercalate between DNA base pairs, and are useful as therapeutic agents against cancer, as assess by an in vitro test of cytotoxicity with human leukemia cells Jurkat E6-1 and human carcinoma cells GLC-4. Preferred compounds are those where -G1 is bonded to -L- through a carbonyl amino and -L-is -(CH2)3NCH3(CH2)3 or -(CH2)2NCH3(CH2)SNCH3(CH2)2- where s = 2 or 3. -G1 is a radical selected from (IIa) y (IIb); -G2 is a radical selected from H, a radical of formula (IIa), a radical of formula (IIb), the N-radical of 1,8-naphthalimide, the C4-radical of 2-phenylquinoline, and the C9-radical of acridine.

  式为G1-L-G2的化合物，其中-G1是结构与cryptolepine接近的基团，-L-是选择自(CH2)rNR''(CH2)s和-(CH2)rNR''(CH2)SNR''(CH2)t的单共价键或共价连接双基团，-R''和-R''是基团，相同或不同，选择自H和(C1-C3)-烷基；r，s和t是1到3之间的整数，-G2是H或结构与-G1接近的基团，是插入剂。它们是插入到DNA碱基对之间的化合物，并且可用作对抗癌症的治疗剂，通过对人类白血病细胞Jurkat E6-1和人类癌细胞GLC-4的体外细胞毒性测试进行评估。优选化合物是那些其中-G1通过一个羰基氨基与-L-结合，-L-是-(CH2)3NCH3(CH2)3或-(CH2)2NCH3(CH2)SNCH3(CH2)2-，其中s = 2或3。-G1是从(IIa)和(IIb)中选择的基团；-G2是从H、式为(IIa)的基团、式为(IIb)的基团、1,8-萘酰亚胺的N-基团、2-苯基喹啉的C4-基团和吖啶的C9-基团中选择的基团。