2-(1,3-dioxo-1,3-dihydro-2H-inden-2-ylidene)hydrazine-1-carboxamide | 114526-85-1

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 2-(1,3-dioxo-1,3-dihydro-2H-inden-2-ylidene)hydrazine-1-carboxamide
• 英文别名: 2-(1,3-dioxo-1H-inden-2(3H)-ylidene)hydrazinecarboxamide；2-semicarbazono-indan-1,3-dione；[(1,3-dioxoinden-2-ylidene)amino]urea
• CAS: 114526-85-1
• 化学式: C₁₀H₇N₃O₃
• 分子量: 217.184
• InChiKey: MHDSHRGZQJKMAH-UHFFFAOYSA-N

物化性质

• 密度：
  1.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 2-(1,3-dioxo-1,3-dihydro-2H-inden-2-ylidene)hydrazine-1-carboxamide 、 ammonium hexafluorophosphate 以 水 为溶剂， 反应 2.0h， 生成 (η⁶-p-cymene)RuCl(k²-N,O-2-(1,3-dioxo-1,3-dihydro-2H-inden-2-ylidene)hydrazine-1-carboxamide)
  参考文献：
  名称：

  Development of highly potent Arene-Ru (II)-ninhydrin complexes for inhibition of cancer cell growth

  摘要：

  In this communication, two new Ru(II)-arene-ninhydrin complexes [(eta(6)-p-cymene)RuCl(k(2)-N,O-2-(1,3-dioxo-1,3-dihydro-2H-inden-2-ylidene)hydrazine-1-carboxamide (Ru-1) and [eta(6)-p-cymene)RuCl(k(2) -N,S-2-(1,3-dioxo-1,3-dihydro-2H-inden-2-ylidene)hydrazine-1-carbothioamide (Ru-2) have been prepared and analyzed by different analytical and spectroscopic techniques. The studies show that Ru(II) complexes have "piano stool" coordination geometry, comprises of one pi-bonded arene centroid, two sigma-bonded nitrogen atoms and one chlorine atom from ninhydrin thiosemicarbazole and Ru(II) metal centre respectively. The molar conductivity study of these complexes in DMSO:water (9:1, v/v) media reveals that complexes are ionic in nature. The photo-physical properties of Ru-1 and Ru-2 with calf thymus deoxyribonucleic acid (CT-DNA) and bovine serum albumin (BSA) were explored. The intrinsic binding constant (K-b) of Ru-1 and Ru-2 with DNA/BSA was found to be 4.5 x 10(5) M-1/1.3 x 10(5) M-1 and 2.1 x 10(5) M-1/1 .2 x 10(5) M-1 respectively. The competitive displacement of ethidium bromide (EtBr) from DNA in the presence of Ru-1 and Ru-2 quantified by quenching constant and viscosity studies. This high binding ability is due to groove binding or intercalation of Ru(II) complexes with CT-DNA which is well supported with in-silico studies. The effect of the Ru-1 and Ru-2 were examined on two different cancer cell lines (HeLa and MDA-MB-231) using the MTT assay. The obtained results show that Ru-1 and Ru-2 exhibits high potency and selectivity with HeLa (IC50 = 9.5 x 10(-6 )mol/L) and MDA-MB-231(IC50 = 14.7 x 10(-6) mol/L) cell lines respectively.

  DOI：

  10.1016/j.ica.2020.119641
• 作为产物：
  描述：

  1,2,3-茚满三酮 、 S-(4-叔-丁基苯甲基)[2-(1-甲基丁基)吡啶-3-基]硫代氨基甲酸酯 在 硫酸 作用下， 以 甲醇 为溶剂， 以89%的产率得到2-(1,3-dioxo-1,3-dihydro-2H-inden-2-ylidene)hydrazine-1-carboxamide
  参考文献：
  名称：

  Development of highly potent Arene-Ru (II)-ninhydrin complexes for inhibition of cancer cell growth

  摘要：

  In this communication, two new Ru(II)-arene-ninhydrin complexes [(eta(6)-p-cymene)RuCl(k(2)-N,O-2-(1,3-dioxo-1,3-dihydro-2H-inden-2-ylidene)hydrazine-1-carboxamide (Ru-1) and [eta(6)-p-cymene)RuCl(k(2) -N,S-2-(1,3-dioxo-1,3-dihydro-2H-inden-2-ylidene)hydrazine-1-carbothioamide (Ru-2) have been prepared and analyzed by different analytical and spectroscopic techniques. The studies show that Ru(II) complexes have "piano stool" coordination geometry, comprises of one pi-bonded arene centroid, two sigma-bonded nitrogen atoms and one chlorine atom from ninhydrin thiosemicarbazole and Ru(II) metal centre respectively. The molar conductivity study of these complexes in DMSO:water (9:1, v/v) media reveals that complexes are ionic in nature. The photo-physical properties of Ru-1 and Ru-2 with calf thymus deoxyribonucleic acid (CT-DNA) and bovine serum albumin (BSA) were explored. The intrinsic binding constant (K-b) of Ru-1 and Ru-2 with DNA/BSA was found to be 4.5 x 10(5) M-1/1.3 x 10(5) M-1 and 2.1 x 10(5) M-1/1 .2 x 10(5) M-1 respectively. The competitive displacement of ethidium bromide (EtBr) from DNA in the presence of Ru-1 and Ru-2 quantified by quenching constant and viscosity studies. This high binding ability is due to groove binding or intercalation of Ru(II) complexes with CT-DNA which is well supported with in-silico studies. The effect of the Ru-1 and Ru-2 were examined on two different cancer cell lines (HeLa and MDA-MB-231) using the MTT assay. The obtained results show that Ru-1 and Ru-2 exhibits high potency and selectivity with HeLa (IC50 = 9.5 x 10(-6 )mol/L) and MDA-MB-231(IC50 = 14.7 x 10(-6) mol/L) cell lines respectively.

  DOI：

  10.1016/j.ica.2020.119641

文献信息

• Derivatives of indan-1,3-dione and indan-1,2,3-trione, methods of
  申请人：Innothera

  公开号：US05571843A1

  公开（公告）日：1996-11-05

  Therapeutic compounds having the formula: ##STR1## in which R.sub.2 and R.sub.3 independently denote H, C.sub.1 -C.sub.4 alkoxy or OH and (A, B)=(oxygen, oxygen) in which case one out of R and R.sub.1 denotes OH, halogen, secondary amino or tertiary amine and the other denotes NHNHCONHR.sub.4 or R and R.sub.1 together denote .dbd.N--NH--CX--NHR.sub.5, .dbd.N--NH--CX--N(phenyl).sub.2, .dbd.N--NH--CX--NH--NH--R.sub.5, .dbd.N--NH--C(SCH.sub.3).dbd.N--R.sub.6 or .dbd.N--N.dbd.C(SCH.sub.3)--NH--R.sub.6 ; or (A, B)=(N--OH, oxygen) in which case R and R.sub.1 together form .dbd.N--NH--CX--NHR.sub.5 or .dbd.N--NH--CX--N(phenyl).sub.2 ; or (A, B)=(N--NH--CX--NHR.sub.5, oxygen) in which case R and R.sub.1 together form .dbd.N--NH--CX--NHR.sub.5 ; or (A, B)=(N--OH, N--OH) in which case R and R.sub.1 together form .dbd.N--NH--CX--NHR.sub.5 or .dbd.N--NH--CX--N(phenyl).sub.2.

  具有以下式子的治疗化合物：##STR1## 其中R.sub.2和R.sub.3分别表示H，C.sub.1-C.sub.4烷氧基或OH，且（A，B）=（氧，氧），此时R和R.sub.1中的一个表示OH，卤素，次级氨基或三级胺基，另一个表示NHNHCONHR.sub.4或R和R.sub.1在一起表示.dbd.N--NH--CX--NHR.sub.5，.dbd.N--NH--CX--N（苯基）.sub.2，.dbd.N--NH--CX--NH--NH--R.sub.5，.dbd.N--NH--C（SCH.sub.3）.dbd.N--R.sub.6或.dbd.N--N.dbd.C（SCH.sub.3）--NH--R.sub.6; 或（A，B）=（N--OH，氧） ，此时R和R.sub.1在一起形成.dbd.N--NH--CX--NHR.sub.5或.dbd.N--NH--CX--N（苯基）.sub.2; 或（A，B）=（N--NH--CX--NHR.sub.5，氧） ，此时R和R.sub.1在一起形成.dbd.N--NH--CX--NHR.sub.5; 或（A，B）=（N--OH，N--OH），此时R和R.sub.1在一起形成.dbd.N--NH--CX--NHR.sub.5或.dbd.N--NH--CX--N（苯基）.sub.2。
• New multicomponent reactions in water: a facile synthesis of 1,3-dioxo-2-indanilidene-heterocyclic scaffolds and indenoquinoxalines through reaction of ninhydrin-malononitrile adduct with diverse <i>N</i>-binucleophiles
  作者：Zahra Rahimi、Mohammad Bayat、Hajar Hosseini

  DOI：10.1039/d2ra06469c

  日期：——

  We report here a highly efficient green approach for the synthesis of imidazolidin-2-ylidene-indenedione, pyrimidine-2-ylidene-indenedione and indenoquinoxaline derivatives through the one-pot three-component reaction between ninhydrin, malononitrile and various diamines in water medium under catalyst-free conditions. High yields (73–98%) of the target products were achieved with short reaction times

  我们在此报道了一种通过茚三酮、丙二腈和各种二胺在水介质中的一锅三组分反应合成咪唑啉-2-亚基-茚二酮、嘧啶-2-亚基-茚二酮和茚并喹喔啉衍生物的高效绿色方法。无催化剂条件。在室温下，反应时间短，目标产物收率高（73-98%）。该方案的显着优点是后处理简单、无需柱色谱、产率良好至优异、反应快速和绿色溶剂。
• REDDY, K. GIRIDHARA;REDDY, K. HUSSAIN;REDDY, D. VENKATA, J. INDIAN INST. SCI., 66,(1986) N 5, 317-323
  作者：REDDY, K. GIRIDHARA、REDDY, K. HUSSAIN、REDDY, D. VENKATA

  DOI：——

  日期：——
• Dérivés d'indane-1,3-dione et d'indane-1,2,3-trione, leurs procédés de préparation et leur application en thérapeutique
  申请人：INNOTHERA

  公开号：EP0566445B1

  公开（公告）日：1996-02-07
• US5571843A
  申请人：——

  公开号：US5571843A

  公开（公告）日：1996-11-05