乙酰乙酸3-(吡啶-3-基)丙酯 | 103839-99-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 中文名称: 乙酰乙酸3-(吡啶-3-基)丙酯
• 英文名称: acetoacetic acid 3-(3-pyridyl)propyl ester
• 英文别名: pyridine-3-yl-propyl-3-oxobutanoate；3-(pyridin-3-yl)propyl 3-oxobutanoate；acetoacetic acid 3-(pyridin-3-yl)propyl ester；3-(pyridin-3-yl)propyl acetoacetate；3-(pyrid-3-yl)-propyl acetoacetate；3-(3-pyridyl)propyl acetoacetate；3-pyridin-3-ylpropyl 3-oxobutanoate
• CAS: 103839-99-2
• 化学式: C₁₂H₁₅NO₃
• 分子量: 221.256
• InChiKey: ZLDMYZSLEMYMLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  56.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酰乙酸3-(吡啶-3-基)丙酯 在 氨 作用下， 以 异丙醇 为溶剂， 反应 175.0h， 生成 4-Isopropyl-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid bis-(3-pyridin-3-yl-propyl) ester
  参考文献：
  名称：

  Newly synthesized dihydropyridine derivatives as modulators of P-Glycoprotein-mediated multidrug resistance

  摘要：

  Newly synthesized 1,4-dihydropyridine derivatives possessing alkyl chains at the 4-position screened whether they could overcome P-glycoprotein-mediated multidrug resistance in cultured cancer cells and also leukemia-bearing animals. Of these derivatives, some could overcome drug resistance to doxorubicin and vincristine in multidrug resistant human cancer cell lines. Combined administration of vincristine and some of the derivatives significantly increased the life span of P-glycoprotein overexpressing multidrug-resistant P388 leukemia-bearing mice. The calcium antagonistic activities, an undesirable effects, were weaker than that of verapamil. These results suggested that the introduction of alkyl groups at the 4-position were effective for both overcoming multidrug resistance and reducing the calcium antagonistic activity. (C) 1998 Elsevier Science Ltd. Al rights reserved.

  DOI：

  10.1016/s0968-0896(98)00170-9
• 作为产物：
  描述：

  双乙烯酮 、 3-吡啶丙醇 以 四氢呋喃 为溶剂， 反应 5.0h， 以78.3%的产率得到乙酰乙酸3-(吡啶-3-基)丙酯
  参考文献：
  名称：

  Newly synthesized dihydropyridine derivatives as modulators of P-Glycoprotein-mediated multidrug resistance

  摘要：

  Newly synthesized 1,4-dihydropyridine derivatives possessing alkyl chains at the 4-position screened whether they could overcome P-glycoprotein-mediated multidrug resistance in cultured cancer cells and also leukemia-bearing animals. Of these derivatives, some could overcome drug resistance to doxorubicin and vincristine in multidrug resistant human cancer cell lines. Combined administration of vincristine and some of the derivatives significantly increased the life span of P-glycoprotein overexpressing multidrug-resistant P388 leukemia-bearing mice. The calcium antagonistic activities, an undesirable effects, were weaker than that of verapamil. These results suggested that the introduction of alkyl groups at the 4-position were effective for both overcoming multidrug resistance and reducing the calcium antagonistic activity. (C) 1998 Elsevier Science Ltd. Al rights reserved.

  DOI：

  10.1016/s0968-0896(98)00170-9

文献信息

• 1,4-dihydropyridines
  申请人：Bayer Aktiengesellschaft

  公开号：US04686229A1

  公开（公告）日：1987-08-11

  1,4-Dihydropyridines of the formula ##STR1## in which R.sup.1 is hydrogen, or alkyl optionally substituted by halogen, nitro, cyano, alkoxy, carboxyl, alkoxycarbonyl or carboxamide, R.sup.2 is hydrogen or alkyl, R.sup.3 is hydrogen, alkyl, carboxyl, alkoxycarbonyl or aryl optionally substituted by hydroxyalkyl, carboxyl, sulphoxy, acloxyalkyl, or ##STR2## R.sup.4 is alkyl, aryl, heteroaryl, aralkyl, heteroaralkyl, ##STR3## X is oxygen, sulphur or NH, and n is 1 to 6, or physiologically acceptable salts thereof, which are active in combating thromboembolic and ischaemic disorders.

  公式为##STR1##的1,4-二氢吡啶，其中R.sup.1是氢，或者由卤素，硝基，氰基，烷氧基，羧基，烷氧羰基或羧酰胺取代的烷基，R.sup.2是氢或烷基，R.sup.3是氢，烷基，羧基，烷氧羰基或芳基，可以由羟基烷基，羧基，磺氧基，乙氧基烷基或##STR2##取代，R.sup.4是烷基，芳基，杂芳基，芳基烷基，杂芳基烷基，##STR3## X是氧，硫或NH，n为1至6，或其生理上可接受的盐，对抗血栓栓塞和缺血性疾病具有活性。
• Reversal of multidrug resistance in cancer cells by novel asymmetrical 1,4-dihydropyridines
  作者：Omidreza Firuzi、Katayoun Javidnia、Elham Mansourabadi、Luciano Saso、Ahmad Reza Mehdipour、Ramin Miri

  DOI：10.1007/s12272-013-0149-8

  日期：2013.11

  many types of cancer. In this study, 14 novel asymmetrical DHPs possessing pyridyl alkyl carboxylate substitutions at C3 and alkyl carboxylate groups at C5 in addition to a nitroimidazole or nitrophenyl moiety at C4 position were synthesized. Calcium channel blocking (CCB) activity was measured in guinea pig ileal longitudinal smooth muscle. Cytotoxicity was tested on 4 human cancer cell lines, while

  多药耐药性 (MDR) 是限制化疗在多种癌症中疗效的重要障碍。在这项研究中，合成了 14 种新型不对称 DHP，除了在 C4 位具有硝基咪唑或硝基苯基部分外，还具有 C3 的吡啶烷基羧酸酯取代和 C5 的烷基羧酸酯基团。在豚鼠回肠纵向平滑肌中测量钙通道阻断 (CCB) 活性。在 4 种人类癌细胞系上测试了细胞毒性，同时对过表达多柔比星抗性 MES-SA-DX5 的 P-糖蛋白的 MDR 逆转能力进行了检查，并与非抗性 MES-SA 细胞进行了比较。化合物显示出不同的 CCB（IC50：29.3 nM–4.75 μM）和细胞毒活性（IC50：6.4 到超过 100 μM）。在C4具有硝基苯基部分的几种化合物，可显着逆转 0.5 和 1 μM 对阿霉素的耐药性。最活跃的是 7e 和 7g，分别在 C5 处含有羧酸乙酯和羧酸异丙酯。7e 和 7g 的 CCB 活性被认为是这些药物的不良反应，分别比硝苯地平低
• 5-Oxo-hexahydroquinoline and 5-oxo-tetrahydrocyclopentapyridine derivatives as promising antiproliferative agents with potential apoptosis-inducing capacity
  作者：Sara Ranjbar、Mehdi Khoshneviszadeh、Marjan Tavakkoli、Ramin Miri、Najmeh Edraki、Omidreza Firuzi

  DOI：10.1007/s11030-021-10281-9

  日期：2022.6

  were tested for antiproliferative effect against three human cancer cell lines including MOLT-4 (acute lymphoblastic leukemia), K562 (chronic myelogenous leukemia), and MCF-7 (breast adenocarcinoma) by MTT assay, and the effect of the most potent derivatives on cell cycle was evaluated by RNase/propidium iodide (PI) flow cytometric assay. Generally, 5-oxo-hexahydroquinoline derivatives (E series) possessed

  发现新型抗癌剂对于扩大癌症患者的治疗选择至关重要。在这项研究中，一系列 49 种 5-氧代-六氢喹啉和 5-氧代-四氢环戊吡啶类似物，在 C 3 处含有不同的吡啶烷基羧酸盐，在 C 4处含有各种脂肪族、芳香族和杂芳香族取代基中央核心的位置，被合成。通过 MTT 法测试了目标化合物对三种人类癌细胞系的抗增殖作用，包括 MOLT-4（急性淋巴细胞白血病）、K562（慢性髓性白血病）和 MCF-7（乳腺癌），以及最有效的作用通过 RNase/碘化丙啶 (PI) 流式细胞术测定衍生物对细胞周期的影响。一般来说，5-氧代-六氢喹啉衍生物（E系列）与其5-氧代-四氢环戊吡啶对应物（F系列）相比具有优越的抗增殖活性。5-氧代-六氢喹啉化合物带有 2-吡啶丙基羧酸酯（D 组）和 3-吡啶丙基羧酸酯（E 组）是比那些带有其他吡啶烷基羧酸酯更好的抗增殖剂。五种具有 IC 的最佳化合物选择针对 MOLT-4 细胞的
• 1,4-dihydropyridine compound and pharmaceutical composition containing
  申请人：Nikken Chemicals Co., Ltd.

  公开号：US05843950A1

  公开（公告）日：1998-12-01

  A 1,4-dihydropyridine compound having the formula (I): ##STR1## wherein, R.sup.1 indicates --COO--A--(3-pyridyl), A indicates a C.sub.3 -C.sub.6 straight chain alkylene group in which one piperazine may be interposed; R.sup.2 indicates a C.sub.2 -C.sub.10 alkyl group, alkenyl group or alkynyl group; a lower alkyl group or lower alkenyl group having a substituent; or a cycloalkyl group which may have a substituent; R.sup.3 indicates the same group as R.sup.1 or --COO--R.sup.4 ; and R.sup.4 indicates a lower alkyl group which may have a substituent or its pharmacologically acceptable salt and an anti-allergenic drug, antiphlogistic, drug for overcoming resistance to anti-cancer drugs, or drug for reinforcing the effect of anti-cancer drugs containing the same as effective ingredients.

  一种具有式（I）的1,4-二氢吡啶化合物：##STR1## 其中，R.sup.1表示--COO--A--（3-吡啶基），A表示C.sub.3-C.sub.6直链烷基，其中可以插入一个哌嗪基; R.sup.2表示C.sub.2-C.sub.10烷基、烯基或炔基；具有取代基的较低烷基或较低烯基；或者可能具有取代基的环烷基；R.sup.3表示与R.sup.1相同的基团或--COO--R.sup.4；R.sup.4表示可能具有取代基的较低烷基或其药理学上可接受的盐，以及包含相同有效成分的抗过敏药物、抗炎药物、克服抗癌药物抵抗力的药物或增强抗癌药物效果的药物。
• 1,4-DIHYDROPYRIDINE COMPOUND AND MEDICINAL COMPOSITION CONTAINING THE SAME
  申请人：Nikken Chemicals Company, Limited

  公开号：EP0801065A1

  公开（公告）日：1997-10-15

  A 1,4-dihydropyridine compound having the formula (I): wherein, R1 indicates -COO-A-(3-pyridyl), A indicates a C3-C6 straight chain alkylene group in which one piperazine may be interposed; R2 indicates a C2-C10 alkyl group, alkenyl group or alkynyl group; a lower alkyl group or lower alkenyl group having a substituent; or a cycloalkyl group which may have a substituent; R3 indicates the same group as R1 or -COO-R4; and R4 indicates a lower alkyl group which may have a substituent or its pharmacologically acceptable salt and an anti-allergenic drug, antiphlogistic, drug for overcoming resistance to anti-cancer drugs, or drug for reinforcing the effect of anti-cancer drugs containing the same as effective ingredients.

  一种具有式（I）的 1，4-二氢吡啶化合物： 其中，R1 表示-COO-A-（3-吡啶基），A 表示 C3-C6 直链亚烷基，其中可插入一个哌嗪；R2 表示 C2-C10 烷基、烯基或炔基；具有取代基的低级烷基或低级烯基；或具有取代基的环烷基；R3 表示与 R1 相同的基团或-COO-R4；R4 表示可能具有取代基的低级烷基或其药理学上可接受的盐，以及作为有效成分的抗过敏药物、抗麻痹药物、克服抗癌药物抗药性的药物或增强抗癌药物效果的药物。