2-amino-5-(pyrrolidin-1-yl)benzamide | 314768-96-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 2-amino-5-(pyrrolidin-1-yl)benzamide
• 英文别名: 2-amino-5-(1-pyrrolidino)-benzamide；2-amino-5-pyrrolidinylbenzamide；Benzamide, 2-amino-5-(1-pyrrolidinyl)-；2-amino-5-pyrrolidin-1-ylbenzamide
• CAS: 314768-96-2
• 化学式: C₁₁H₁₅N₃O
• 分子量: 205.26
• InChiKey: PKNIRARSTODNBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  72.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-amino-5-(pyrrolidin-1-yl)benzamide 在 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.08h， 生成 N-(tert-butyl)-2-(3-(4-oxo-6-(pyrrolidin-1-yl)-3,4-dihydroquinazolin-2-yl)phenoxy)acetamide
  参考文献：
  名称：

  [EN] GLUCOSE UPTAKE INHIBITORS
  [FR] INHIBITEURS DE L'ABSORPTION DU GLUCOSE

  摘要：

  这项发明提供了一种调节葡萄糖摄取活性和细胞对葡萄糖的运输/摄取的化合物，尤其是GLUTS3，但也包括但不限于GLUT1-14（SLC2A1-SLC2A14）。发明中的化合物可用于治疗包括癌症、自身免疫性疾病和炎症、感染性疾病以及代谢性疾病。

  公开号：

  WO2020005935A1
• 作为产物：
  描述：

  2-nitro-5-(pyrrolidin-1-yl)benzamide 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 2-amino-5-(pyrrolidin-1-yl)benzamide
  参考文献：
  名称：

  6-吡咯烷基-2-(2-取代苯基)-4-喹唑啉酮的合成及细胞毒性

  摘要：

  在我们继续寻找潜在的抗癌候选药物时，选择了 2-(3-甲氧基苯基)-6-吡咯烷基-4-喹唑啉酮 (JJC-1) 作为先导化合物。起始 5-吡咯烷基-2-氨基苯甲酰胺使用标准方法由 5-氯-2-硝基苯甲酸通过与 SOCl2、NH3、吡咯烷和 H2 反应制备。然后在 NaHSO3 存在下，在 N,N-二甲基乙酰胺 (DMAC) 中使起始苯甲酰胺与 2-取代苯甲醛或苯甲酰氯在 150 °C 下反应。热环脱水/脱氢得到目标 6-吡咯烷基-2-(2-取代的苯基)-4-喹唑啉酮 (15-22)。这些目标化合物在体外对六种癌细胞系进行了细胞毒性分析，包括人单核细胞白血病细胞 (U937)、小鼠单核细胞白血病细胞 (WEHI-3)、人肝癌细胞 (HepG2、Hep3B) 和人肺癌细胞 (A549, CH27)。它们中的大多数对U937和WEHI-3细胞表现出显着的细胞毒作用，EC50值范围为0.30至10

  DOI：

  10.1002/jccs.200700113

文献信息

• 2-phenyl-4-quinazolinone compounds, 2-phenyl-4-alkoxy-quinazoline compounds and their pharmaceutical compositions
  申请人：National Science Council

  公开号：US06479499B1

  公开（公告）日：2002-11-12

  Two series of 6,7,2′,3′,4′,5′-substituted 2-phenyl-4-quinazolinones and 6,2′,3′,4′,5′-substituted 2,3-dihydro-2-phenyl-4-quinazolinones are synthesized and evaluated for cytotoxicity against a panel of human tumor cell lines, such as epidermoid carcinoma of the nasopharynx (KB), lung carcinoma (A-549), ileocecal carcinoma (HCT-8), breast cancer (MCF-7), melanoma (SKMEL-2), ovarian cancer (1A9), glioblastoma (U-87-MG), bone (HOS), P-gp-expressing epidermoid carcinoma of the nasopharynx (KB-VIN), and prostate cancer (PC3) cell lines, and some of the compounds are found potent. The present invention also synthesizes 2-phenyl-4-alkoxy-quinazoline compounds, wherein some of the compounds exhibit antiplatelet activity.

  合成了两种系列的化合物，分别是6,7,2′,3′,4′,5′-取代的2-苯基-4-喹唑啉酮和6,2′,3′,4′,5′-取代的2,3-二氢-2-苯基-4-喹唑啉酮，并评价了它们对人肿瘤细胞系如鼻咽癌上皮细胞癌（KB）、肺癌（A-549）、回肠癌（HCT-8）、乳腺癌（MCF-7）、黑色素瘤（SKMEL-2）、卵巢癌（1A9）、胶质母细胞瘤（U-87-MG）、骨肉瘤（HOS）、表达P-gp的鼻咽癌上皮细胞癌（KB-VIN）和前列腺癌（PC3）细胞系的细胞毒性，发现其中一些化合物具有显著的活性。本发明还合成了2-苯基-4-烷氧基喹唑啉化合物，其中一些化合物显示出抗血小板活性。
• 2-Aryl-4-Quinazolinones And Their Pharmaceutical Compositions
  申请人：Hour Mann-Jen

  公开号：US20130102602A1

  公开（公告）日：2013-04-25

  Provided is a compound of the formula I or a pharmaceutically acceptable salt, solvate or stereoisomer thereof: wherein Ar represents R 5 , R 6 , R 7 , R 8, R 1 ′, R 2 ′, R 3 ′, R 4 ′, R 5 ′, R 6 ′, R 7 ′, R 8 ′ independently represent H, OH, F, Cl, Br, C 1 to C 6 alkyl group, C 1 to C 6 alkoxy group, C 2 to C 6 alkenyl group, C 2 to C 6 alkenoxy group, C 2 to C 6 alkynyl group, C 2 to C 6 alkynoxy group, amine group, mono- or di-substituted amino group, cyclic C 1 to C 5 alkylamino group, imidazolyl group, morpholino group, piperazinyl group, optionally substituted with one or more hydroxy or halo; and X represents NH, O or S. The present invention also provides a composition comprising the compound of formula I. The compound and the composition in accordance with the present invention are effective on treating or alleviating a disease or disorder, such as malignant glioma.

  提供的是公式I的化合物或其药用可接受的盐、溶剂化物或立体异构体：其中Ar代表R5、R6、R7、R8、R1'、R2'、R3'、R4'、R5'、R6'、R7'、R8'独立代表H、OH、F、Cl、Br、C1至C6烷基团、C1至C6烷氧基团、C2至C6烯基团、C2至C6烯氧基团、C2至C6炔基团、C2至C6炔氧基团、氨基团、单或二取代氨基团、环状C1至C5烷基氨团、咪唑基团、吗啡啉基团、哌嗪基团，可选择地被一个或多个羟基或卤素取代；X代表NH、O或S。本发明还提供了包含公式I化合物的组合物。根据本发明的化合物和组合物对治疗或缓解疾病或病症有效，如恶性胶质瘤。
• Synthesis and Cytotoxicity of 6-Pyrrolidinyl-2-(2-Substituted Phenyl)-4-Quinazolinones
  作者：Mann-Jen Hour、Jai-Sing Yang、Jin-Cherng Lien、Sheng-Chu Kuo、Li-Jiau Huang

  DOI：10.1002/jccs.200700113

  日期：2007.6

  and H2. The starting benzamide then was reacted with 2-substituted benzaldehyde or benzoyl chloride in N,N-dimethylacetamide (DMAC) in the presence of NaHSO3 at 150 °C. Thermal cyclodehydration/dehydrogenation gave the target 6-pyrrolidinyl-2-(2-substituted phenyl)-4-quinazolinones (15–22). These target compounds were assayed for their cytotoxicity in vitro against six cancer cell lines, including human

  在我们继续寻找潜在的抗癌候选药物时，选择了 2-(3-甲氧基苯基)-6-吡咯烷基-4-喹唑啉酮 (JJC-1) 作为先导化合物。起始 5-吡咯烷基-2-氨基苯甲酰胺使用标准方法由 5-氯-2-硝基苯甲酸通过与 SOCl2、NH3、吡咯烷和 H2 反应制备。然后在 NaHSO3 存在下，在 N,N-二甲基乙酰胺 (DMAC) 中使起始苯甲酰胺与 2-取代苯甲醛或苯甲酰氯在 150 °C 下反应。热环脱水/脱氢得到目标 6-吡咯烷基-2-(2-取代的苯基)-4-喹唑啉酮 (15-22)。这些目标化合物在体外对六种癌细胞系进行了细胞毒性分析，包括人单核细胞白血病细胞 (U937)、小鼠单核细胞白血病细胞 (WEHI-3)、人肝癌细胞 (HepG2、Hep3B) 和人肺癌细胞 (A549, CH27)。它们中的大多数对U937和WEHI-3细胞表现出显着的细胞毒作用，EC50值范围为0.30至10
• 2-ARYL-4-QUINAZOLINONES AND THEIR PHARMACEUTICAL COMPOSITIONS
  申请人：China Medical University

  公开号：US20130310376A1

  公开（公告）日：2013-11-21

  Provided is a compound of the formula I or a pharmaceutically acceptable salt, solvate or stereoisomer thereof: wherein Ar represents R 5 , R 7 , R 8 , R 2 ′, R 3 ′, R 4 ′, R 5 ′, R 6 ′, R 7 ′, R 8 ′ independently represent H, OH, F, Cl, Br methoxyl group, NH 2 group or NMe 2 group; X represents NH, O or S; R 6 is selected from the group consisting of: piperidinyl group, morpholino group, methoxyl group, and dimethylamine group. The present invention also provides a composition comprising the compound of formula I. The compound and the composition in accordance with the present invention are effective on treating or alleviating a disease or disorder, such as malignant glioma.

  提供的是公式I的化合物或其药学上可接受的盐、溶剂或立体异构体，其中Ar代表R5、R7、R8、R2'、R3'、R4'、R5'、R6'、R7'、R8'，分别独立地表示H、OH、F、Cl、Br、甲氧基基团、NH2基团或NMe2基团；X代表NH、O或S；R6选自以下组中的一种：哌啶基团、吗啉基团、甲氧基基团和二甲胺基团。本发明还提供了一种包含公式I化合物的组合物。根据本发明，该化合物和组合物对于治疗或缓解疾病或障碍，如恶性胶质瘤，具有良好的疗效。
• 6-Alkylamino- and 2,3-Dihydro-3‘-methoxy-2-phenyl-4-quinazolinones and Related Compounds:  Their Synthesis, Cytotoxicity, and Inhibition of Tubulin Polymerization
  作者：Mann-Jen Hour、Li-Jiau Huang、Sheng-Chu Kuo、Yi Xia、Kenneth Bastow、Yuka Nakanishi、Ernest Hamel、Kuo-Hsiung Lee

  DOI：10.1021/jm000151c

  日期：2000.11.1

  As part of our continuing search for potential anticancer candidates among 2-phenyl-4-quinolones and 2-phenyl-4-quinazolinones, two series of 6,7,2',3',4',5'-substituted 2-phenyl-4-quinazolinones and 6,2',3',4',5'-substituted 2,3-dihydro-2-phenyl-4-quinazolinones were synthesized and evaluated for cytotoxicity and as inhibitors of tubulin polymerization. In general, a good correlation was found between the two activities. Five of the 6-substituted heterocyclic 2-phenyl-4-quinozolinones (37-51) showed significant cytotoxicity against a panel of human tumor cell lines with EC50 values in the low micromolar to nanomolar concentration ranges. Compound 38 was the most potent of these compounds, as well as the most potent inhibitor of tubulin polymerization in this series. The activity of 38 was in the same range as those of the antimitotic natural products, colchicine, podophyllotoxin, and combretastatin A-4. Substituted 2-phenyl-4-quinazolinones and 2,3-dihydro-2-phenyl-4-quinazolinones also displayed highly selective cytotoxicity against the ovarian cancer 1A9 and P-gp resistant KB-VIN cell lines.