4-(pyrrolidin-1-yl)-2-thioxo-1,2-dihydropyridine-3-carbonitrile | 868062-44-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-(pyrrolidin-1-yl)-2-thioxo-1,2-dihydropyridine-3-carbonitrile
• 英文别名: 4-pyrrolidin-1-yl-2-thioxo-1,2-dihydropyridine-3-carbonitrile；4-pyrrolidin-1-yl-2-sulfanylidene-1H-pyridine-3-carbonitrile
• CAS: 868062-44-6
• 化学式: C₁₀H₁₁N₃S
• 分子量: 205.283
• InChiKey: GOMBDBJIOBDZSG-UHFFFAOYSA-N

物化性质

• 沸点：
  271.8±50.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  71.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(pyrrolidin-1-yl)-2-thioxo-1,2-dihydropyridine-3-carbonitrile 在 sodium methylate 、 sodium carbonate 、 hydroxylamine-O-sulfonic acid 作用下， 以 甲醇 、 水 为溶剂， 反应 0.25h， 以51%的产率得到2-aminosulfanyl-4-(pyrrolidin-1-yl)-pyridine-3-carbonitrile
  参考文献：
  名称：

  2-Mercapto-4-(pyrrolidin-1-yl)pyridine-3-carbonitrile 衍生物的合成及微生物活性

  摘要：

  描述了从 2-溴-4-(pyrrolidin-1-yl)pyridine-3-carbonitrile (1) 开始合成 2-mercapto-4-(pyrrolidin-1-yl)pyridine 衍生物。1 与合适的苯硫酚反应得到所需的 2-(苯硫基)-4-(吡咯烷-1-基)吡啶-3-甲腈衍生物，而与苄硫醇反应得到相关的噻吩基衍生物。或者，将化合物 1 转化为 2-巯基-4-(吡咯烷-11-基)吡啶-3-甲腈 (2)。2 与氯乙酸或氯丙酮衍生物反应得到巯基取代的相关产物。后一种化合物可以在索普-齐格勒反应中环化为相关的 3-氨基-4-(吡咯烷-1-基)噻吩并[2,3-b]吡啶衍生物。2与羟氨基-O-磺酸钠反应得到相关的氨基硫烷基衍生物。

  DOI：

  10.3987/com-08-11390
• 作为产物：
  描述：

  1,1-dicyano-4-(N,N-dimethylamino)-2-methoxy-1,3-butadiene 在 氢溴酸 、 溶剂黄146 、 硫脲 作用下， 以 甲醇 为溶剂， 反应 26.67h， 生成 4-(pyrrolidin-1-yl)-2-thioxo-1,2-dihydropyridine-3-carbonitrile
  参考文献：
  名称：

  The Synthesis and Antibacterial Activity of Novel 4-Pyrrolidin-3-cyanopyridine Derivatives

  摘要：

  2-Bromo-4-(pyrrolidin-1-yl)pyridine-3-carbonitrile obtained from 2-(1,3-bis(pyrrolidin-1-yl)allylidene)malononitrile has been used as a substrate for the synthesis of new cyanopyridine derivatives: 2-methoxy, 2-phenoxy, 2-aminoethylthio, and 2-thioxo. 4-(Pyrrolidin-1-yl)-2-thioxo-1,2-dihydropyridine-3-carbonitrile 7 in reaction with suitable alkyl and aminoalkyl halides gave respective sulfides. All synthesized compounds were evaluated for their antimicrobial activity against 26 aerobic and anaerobic bacteria. Determined minimal inhibitory concentration values ranged from 6.2 to 100 mu g/mL. Derivatives 1, 3, 4, 6, and 12 were the most active compounds.

  DOI：

  10.1002/jhet.1518

文献信息

• THIENOPYRIDINE DERIVATIVES
  申请人：Sankyo Company, Limited

  公开号：EP1764367A1

  公开（公告）日：2007-03-21

  The present invention provides a compound promoting osteogenesis. The present invention provides a compound having the following general formula (I) wherein R1 is H or alkyl, R2 is RaS-, RaO-, RaNH-, Ra(Rb)N- or cyclic amino, and Ra and Rb are alkyl which may be substituted, cycloalkyl which may be substituted, or the like, or a pharmacologically acceptable salt thereof.

  本发明提供一种促进成骨的化合物。本发明提供具有以下一般式（I）的化合物 其中R1为H或烷基， R2为RaS-、RaO-、RaNH-、Ra(Rb)N-或环状氨基，且 Ra和Rb为可以被取代的烷基、可以被取代的环烷基等，或其药理学上可接受的盐。
• Discovery and structure–activity relationship of thienopyridine derivatives as bone anabolic agents
  作者：Keiji Saito、Akira Nakao、Tsuyoshi Shinozuka、Kousei Shimada、Satoshi Matsui、Kiyoshi Oizumi、Kazuki Yano、Keiko Ohata、Daisuke Nakai、Yoko Nagai、Satoru Naito

  DOI：10.1016/j.bmc.2013.01.071

  日期：2013.4

  A cell-based assay was performed for the discovery of novel bone anabolic agents. Alkaline phosphatase (ALPase) activity of ST2 cells was utilized as an indicator of osteoblastic differentiation, and thienopyridine derivative 1 was identified as a hit compound. 3-Aminothieno[2,3-b]pyridine-2-carboxamide was confirmed to be a necessary core structure for the enhancement of ALPase activity, and then

  进行了基于细胞的测定，以发现新型骨合成代谢剂。ST2细胞的碱性磷酸酶（ALPase）活性被用作成骨细胞分化的指标，噻吩并吡啶衍生物1被确定为命中化合物。确认3-氨基噻吩并[2，3- b ]吡啶-2-甲酰胺是增强ALPase活性的必要核心结构，然后对噻吩并吡啶环上的C4-取代基进行了优化。将环氨基引入噻吩并吡啶环的C4位提高了活性。特别地，在该新系列中，发现N-苯基-高哌嗪衍生物是ALPase的强增强剂。此外，3-氨基-4-（4-苯基-1,4-二氮杂-1-基）噻吩并[2,3-在6周内向卵巢切除（OVX）大鼠口服b ]吡啶-2-甲酰胺（15k）以评估其对面骨矿物质密度（aBMD）的影响，并且从10 mg / mg的剂量观察到aBMD有统计学上的显着改善公斤/天。
• Thienopyridine Derivatives
  申请人：Oizumi Kiyoshi

  公开号：US20070219234A1

  公开（公告）日：2007-09-20

  [Problem to be Solved]The present invention provides a compound promoting osteogenesis. [Solution] The present invention provides a compound having the following general formula (I) wherein R 1 is H or alkyl, R 2 is R a S—, R a O—, R a NH—, R a (R b )N— or cyclic amino, and R a and R b are alkyl which may be substituted, cycloalkyl which may be substituted, or the like, or a pharmacologically acceptable salt thereof.

  【待解决的问题】本发明提供了一种促进成骨作用的化合物。 【解决方案】本发明提供了一种具有以下通式（I）的化合物，其中R1为H或烷基，R2为RaS—、RaO—、RaNH—、Ra（Rb）N—或环状氨基，而Ra和Rb为可被取代的烷基、可被取代的环烷基等，或其药理学上可接受的盐。
• The Synthesis and Antibacterial Activity of Novel 4-Pyrrolidin-3-cyanopyridine Derivatives
  作者：Agnieszka Bogdanowicz、Henryk Foks、Katarzyna Gobis、Anna Kędzia、Ewa Kwapisz、Andrzej Olczak、Marek L. Główka

  DOI：10.1002/jhet.1518

  日期：2013.5

  2-Bromo-4-(pyrrolidin-1-yl)pyridine-3-carbonitrile obtained from 2-(1,3-bis(pyrrolidin-1-yl)allylidene)malononitrile has been used as a substrate for the synthesis of new cyanopyridine derivatives: 2-methoxy, 2-phenoxy, 2-aminoethylthio, and 2-thioxo. 4-(Pyrrolidin-1-yl)-2-thioxo-1,2-dihydropyridine-3-carbonitrile 7 in reaction with suitable alkyl and aminoalkyl halides gave respective sulfides. All synthesized compounds were evaluated for their antimicrobial activity against 26 aerobic and anaerobic bacteria. Determined minimal inhibitory concentration values ranged from 6.2 to 100 mu g/mL. Derivatives 1, 3, 4, 6, and 12 were the most active compounds.
• The Synthesis and Microbiological Activity of 2-Mercapto-4-(pyrrolidin-1-yl)pyridine-3-carbonitrile Derivatives
  作者：Agnieszka Miszke、Henryk Foks、Anna Kedzia、Ewa Kwapisz、Zofia Zwolska

  DOI：10.3987/com-08-11390

  日期：——

  chloroacetone derivatives gave related products of mercapto group substitution. The latter compounds could be cyclized in Thorpe-Ziegler reaction to related 3-amino-4-(pyrrolidin-1-yl)thieno[2,3-b]pyridine derivatives. Reaction of 2 with sodium hydroxylamino-O-sulphonate gave the related aminosulfanyl derivative. Selected product were screened for bacteriostatic and antituberculosis activity, and some of them

  描述了从 2-溴-4-(pyrrolidin-1-yl)pyridine-3-carbonitrile (1) 开始合成 2-mercapto-4-(pyrrolidin-1-yl)pyridine 衍生物。1 与合适的苯硫酚反应得到所需的 2-(苯硫基)-4-(吡咯烷-1-基)吡啶-3-甲腈衍生物，而与苄硫醇反应得到相关的噻吩基衍生物。或者，将化合物 1 转化为 2-巯基-4-(吡咯烷-11-基)吡啶-3-甲腈 (2)。2 与氯乙酸或氯丙酮衍生物反应得到巯基取代的相关产物。后一种化合物可以在索普-齐格勒反应中环化为相关的 3-氨基-4-(吡咯烷-1-基)噻吩并[2,3-b]吡啶衍生物。2与羟氨基-O-磺酸钠反应得到相关的氨基硫烷基衍生物。