1-benzylspiro-4'-one | 76857-06-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-benzylspiro-4'-one
• 英文别名: 1-benzylspiro-4'-one；1-benzylspiro4'-one；1-benzyl-1'H-spiro[piperidine-4,2'-quinazolin]-4'(3'H)-one；1-benzylspiro[piperidine-4,2'(1'H)-quinazolin]-4'(3'H)-one；1-benzylspiro[piperidine-4, 2'-(1',2',3',4'-tetrahydroquinazolin)]-4'-one；1-benzyl-2',3'-dihydrospiro[piperidine-4,2'-quinazoline]-4'(1'H)-one；1'-benzylspiro[1,3-dihydroquinazoline-2,4'-piperidine]-4-one
• CAS: 76857-06-2
• 化学式: C₁₉H₂₁N₃O
• mdl: MFCD06200213
• 分子量: 307.395
• InChiKey: QYQMLXUZPUNBGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.315
• 拓扑面积：
  44.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-benzylspiro-4'-one 在 吡啶 、 lithium aluminium tetrahydride 、 磺酰胺 作用下， 以 1,4-二氧六环 为溶剂， 生成 1-benzyl-4-(3,4-dihydro-2,2-dioxo-1H-2,1,3-benzothiadiazin-1-yl)piperidine
  参考文献：
  名称：

  [EN] DIPHENYLBUTYPIPERIDINE AUTOPHAGY INDUCERS
  [FR] INDUCTEURS, À BASE DE DIPHÉNYLBUTYLPIPÉRIDINE, DE L'AUTOPHAGIE

  摘要：

  公开号：

  WO2011143444A3
• 作为产物：
  描述：

  N-苄基哌啶酮 、 2-氨基苯甲酰胺 在 硫酸 、 溶剂黄146 作用下， 以49%的产率得到1-benzylspiro-4'-one
  参考文献：
  名称：

  Synthesis and Evaluation as NOP Ligands of Some Spiro[piperidine-4,2'(1'H)-quinazolin]-4'(3'H)-ones and Spiro[piperidine-4,5'(6'H)-[1,2,4]triazolo[1,5-c]quinazolines]

  摘要：

  合成了一些螺[哌啶-4,2′(1′H)-喹唑啉]-4′(3′H)-酮 3 和螺[哌啶-4,5′(6′H)-[1,2,4]三唑[1,5-c]喹唑啉] 4，并评估其作为疼痛受体配体的活性。所检验的化合物显示出部分激动活性，除了化合物 3 和 4n，这两者被证明是纯拮抗剂。

  DOI：

  10.1248/cpb.54.611

文献信息

• SPIRO COMPOUND AND USE THEREOF
  申请人：Taniguchi Takahiko

  公开号：US20100069351A1

  公开（公告）日：2010-03-18

  The present invention aims to provide a novel SCD inhibitor. The present invention relate to SCD inhibitor comprising A compound represented by the formula (I) wherein R is an optionally substituted cyclic group or an optionally substituted carbamoyl group, provided that R is not an optionally substituted 7-pyrido[2,3-d]pyrimidyl group; ring A is an optionally further substituted pyridazine ring; R 1 , R 2 , R 3 , R 4 , R 11 , R 12 , R 13 and R 14 are each independently a hydrogen atom or a substituent, or R 1 and R 11 in combination, R 2 and R 12 in combination, R 3 and R 13 in combination, or R 4 and R 14 in combination optionally form an oxo group, or R 2 and R 4 in combination optionally form a bond or an alkylene cross-linkage; m and n are each independently an integer of 0 to 2; ring B is an optionally substituted ring, provided that the two atoms constituting ring B, which are adjacent to the spiro carbon atom, are not oxygen atoms at the same time, or a salt thereof, or a prodrug thereof.

  本发明旨在提供一种新型SCD抑制剂。本发明涉及一种包括下式（I）所表示的化合物的SCD抑制剂：其中R是一个可选择取代的环基或可选择取代的氨甲酰基，但R不是一个可选择取代的7-吡啶并[2,3-d]嘧啶基团；环A是一个可选择进一步取代的吡啶并嘧啶环；R1、R2、R3、R4、R11、R12、R13和R14分别独立地是氢原子或取代基，或R1和R11的组合体，R2和R12的组合体，R3和R13的组合体，或R4和R14的组合体可选择形成氧基，或R2和R4的组合体可选择形成键或烷基交联；m和n分别独立地是0到2的整数；环B是一个可选择取代的环，但构成环B的两个与螺碳原子相邻的原子不同时为氧原子，或其盐，或其前药。
• Facile Method for the Combinatorial Synthesis of 2,2-Disubstituted Quinazolin-4(1<i>H</i>)-one Derivatives Catalyzed by Iodine in Ionic Liquids
  作者：Xiang-Shan Wang、Ke Yang、Jie Zhou、Shu-Jiang Tu

  DOI：10.1021/cc900174p

  日期：2010.7.12

  A mild and facile method for the combinatorial synthesis of quinazolin-4-(1H)-one derivatives, containing simple 2,2-disubstituted quinazolin-4-(1H)-ones, spirocyclic quinazolin-4-(1H)-ones, spiro-heterocyclic quinazolin-4-(1H)-ones, and dispirocyclic quinazolin-4-(1H)-ones, is described, which results in high yields by using ionic liquids as green media. The method involves the reaction of 2-aminobenzamides

  为喹唑啉4-（1的组合合成的温和和容易的方法ħ） -酮衍生物，含有简单2,2-二取代的喹唑啉4-（1 ħ） -酮，螺喹唑啉4-（1- ħ） -的，螺-杂环喹唑啉4-（1 ħ） -酮，和dispirocyclic喹唑啉4-（1 ħ） -酮，描述，其结果以高收率通过使用离子液体作为绿色介质。该方法涉及2-氨基苯甲酰胺与碘催化的各种酮的反应，并提供了用于生物医学筛选的新的喹唑啉-4-（1 H）-一文库。
• Synthesis of 1- and 3-(1-substituted 4-piperidinyl)-1,2,3,4-tetrahydro-2-oxoquinazolines as potential antihypertensive agents.
  作者：HARUKI TAKAI、HIROYUKI OBASE、NOBUHIRO NAKAMIZO、MASAYUKI TERANISHI、KAZUHIRO KUBO、KATSUICHI SHUTO、YUTAKA KASUYA、KOKI SHIGENOBU、MAKIKO HASHIKAMI、NAOKO KARASHIMA

  DOI：10.1248/cpb.33.1116

  日期：——

  A series of 1-and 3-(1-substituted 4-piperidinyl)-1, 2, 3, 4-tetrahydro-2-oxoquinazolines were synthesized and tested for antihypertensive activity. Among the compounds tested, 1-(2-hydroxy-2-phenethyl)-4-(1, 2, 3, 4-tetrahydro-2-oxo-3-quinazolinyl) piperidine derivatives were generally the most effective in lowering blood pressure in the spontaneous hypertensive rat model. Of these, 1-[2-(4-chlorophenyl)-2-hydroxyethyl]-4-(1, 2, 3, 4-tetrahydro-2-oxo-3-quinazolinyl) piperidine (26) (KF5908) seemed the most promising.

  合成了一系列1-和3-(1-取代4-哌啶基)-1, 2, 3, 4-四氢-2-酮喹唑啉，并测试了它们的抗高血压活性。在测试的化合物中，1-(2-羟基-2-苯乙基)-4-(1, 2, 3, 4-四氢-2-酮-3-喹唑啉基)哌啶衍生物通常在自发性高血压大鼠模型中降低血压的效果最佳。其中，1-[2-(4-氯苯基)-2-羟基乙基]-4-(1, 2, 3, 4-四氢-2-酮-3-喹唑啉基)哌啶（26）（KF5908）似乎最具前景。
• Synthesis and evaluation of anticancer and PDE 5 inhibitory activity of spiro-substituted quinazolin-4-ones
  作者：Mohamed A. Ameen、Essam Kh. Ahmed、Mohamed Ramadan、Hisham A. Abd El-Naby、Asmaa A. Abdel-Haseeb

  DOI：10.1007/s00706-017-1961-5

  日期：2017.8

  spectral analysis, screened for their anticancer activity at a concentration of 10 μΜ against a panel of 56 cell lines derived from nine different types of cancers, including leukemia, melanoma, lung, colon, CNS, ovarian, renal, prostate, and breast cancers. The synthesized compounds screened for their PDE 5 inhibitory activity and it showed encouraged activity compared to sildenafil. Graphical abstract

  摘要合成了一系列新颖的螺取代的2,3-二氢喹唑啉-4（1 H）-酮，并通过光谱分析在结构上进行了确认，以10μM的浓度筛选了它们对一组源自9种细胞的56种细胞系的抗癌活性不同类型的癌症，包括白血病，黑素瘤，肺癌，结肠癌，中枢神经系统，卵巢癌，肾癌，前列腺癌和乳腺癌。合成的化合物筛选了其PDE 5抑制活性，与西地那非相比显示出令人鼓舞的活性。 图形概要
• Reaction of spiro[piperidine-4,2'-(1',2',3',4'-tetrahydroquinazolin)]-4'-ones with acid anhydrides.
  作者：MASATOSHI YAMATO、JIROH HORIUCHI、YASUO TAKEUCHI

  DOI：10.1248/cpb.28.2623

  日期：——

  Acylation of spiro[piperidine-4, 2'-(1', 2', 3', 4'-tetrahydroquinazolin)]-4'-ones (1d, 4, 6, and 7) was attempted. In all cases, the resulting products were not the corresponding acyl derivatives but two types of products (2 or 3 and 5). Heating 1d, the derivative having hydrogen atoms on the N(1) and N(3)-positions of spiro[piperidine-4, 2'-(1', 2', 3', 4'-tetrahydroquinazolin)]-4'-ones with acetic anhydride or benzoic anhydride gave 1-(1-benzyl-1, 2, 5, 6-tetrahydro-4-pyridyl)-2-methyl-1, 4-dihydroquinazolin-4-one (2) or 1-(1-benzyl-1, 2, 5, 6-tetrahydro-4-pyridyl)-2-methyl-1, 4-dihydroquinazolin-4-one (3), respectively. On the other hand, heating 4, the N(1)-substituted derivative of 1d, with acetic anhydride gave 2-benzyl-5-methyl-1, 2, 3, 4, 5, 10-hexahydro-benzo[b]-1, 6-naphthyridin-10-one (5). The N(3)-substituted derivatives (6 and 7) of 1d did not react with acetic anhydride.

  尝试将螺[哌啶-4, 2'-(1', 2', 3', 4'-四氢喹唑啉)]-4'-酮(1d、4、6和7)酰化。在所有情况下，所得产物都不是相应的酰基衍生物，而是两种类型的产物（2或3和5）。加热1d，得到螺[哌啶-4,2'-(1',2',3',4'-四氢喹唑啉)]-4'的N(1)和N(3)位上有氢原子的衍生物-与乙酸酐或苯甲酸酐反应生成1-(1-苄基-1,2,5,6-四氢-4-吡啶基)-2-甲基-1,4-二氢喹唑啉-4-酮(2)或1- (1-苄基-1,2,5,6-四氢-4-吡啶基)-2-甲基-1,4-二氢喹唑啉-4-酮(3)。另一方面，将1d的N(1)-取代衍生物4与乙酸酐加热，得到2-苄基-5-甲基-1,2,3,4,5,10-六氢-苯并[b]- 1、6-萘啶-10-一(5)。 1d的N(3)-取代衍生物(6和7)不与乙酸酐反应。