(E)-2-(2,3-dihydro-1H-inden-1-ylidene)hydrazine-1-carbothioamide | 909248-50-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (E)-2-(2,3-dihydro-1H-inden-1-ylidene)hydrazine-1-carbothioamide
• 英文别名: (E)-1-(1,2-dihydroinden-3-ylidene)thiosemicarbazide；1-(2,3-Dihydroinden-1-ylidene)thiosemicarbazide；[(E)-2,3-dihydroinden-1-ylideneamino]thiourea
• CAS: 909248-50-6
• 化学式: C₁₀H₁₁N₃S
• 分子量: 205.283
• InChiKey: WFHFUKVEUQNVSI-FMIVXFBMSA-N

物化性质

• 沸点：
  368.5±35.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  82.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-2-(2,3-dihydro-1H-inden-1-ylidene)hydrazine-1-carbothioamide 、 2-氯乙酰乙酸乙酯 在 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以65%的产率得到(E)-5-acetyl-2-{[(E)-2,3-dihydro-1H-inden-1-ylidene]hydrazono}thiazolidin-4-one
  参考文献：
  名称：

  Synthesis of some new thiazole derivatives and their cytotoxicity on different human tumor cell lines

  摘要：

  Some novel 1-(inden-3-ylidene)-2-(thiazol-2-ylidene) hydrazine derivatives 3-9 were synthesized by the Hantzsch reaction of thiosemicarbazone derivatives 2a-2c with halo ketones and halo esters. Thiosemicarbazone derivatives reacted with hydrozonyl chlorides to give diazenyl-4-methylthiazole derivatives 11a-11d. Structures of the products were elucidated from IR, H-1, and C-13 NMR, and Mass spectra elucidate. The synthesized compounds were screened for their cytotoxicity against three human tumor cell lines. Twenty compounds showed high (>= 60 %) antiproliferative activity over breast cancer (MCF-7). Compounds 2b, 3c, 4a, 4b, 6b, 6c, 7b, 8a, and 11b possessed higher cytotoxic activity over breast tumor cell line than Doxorubicin.

  DOI：

  10.1134/s1070363217100218
• 作为产物：
  描述：

  氨基硫脲 、 1-茚酮 在 盐酸 作用下， 以 乙醇 为溶剂， 生成 (E)-2-(2,3-dihydro-1H-inden-1-ylidene)hydrazine-1-carbothioamide
  参考文献：
  名称：

  新型噻唑肼衍生物的合成、表征及其对 VEGFR-2 的抑制作用

  摘要：

  摘要 目的：新型噻唑肼衍生物的合成、表征及其对 VEGFR-2 的抑制作用。方法：采用3-(4,5-二甲基噻唑-2-基)-2,5-二苯基溴化四唑(MTT)测定法评价新型合成衍生物体外抑制癌细胞生长的能力。结果和讨论：合成的衍生物对所选癌细胞系具有中等至显着的体外抗癌活性。化合物 ( Va )、( Vb ) 和 ( Ve ) 表现出显着的抗癌活性，IC 50值为 10.24–15.44 µM。结论：其中，与其他测试化合物相比，化合物 ( Va )、( Vb ) 和 ( Ve ) 显示出最有效的抑制作用。因此，目前的研究报告表明，噻唑肼衍生物将来可以开发为有利的抗癌实体。

  DOI：

  10.1134/s1068162024020067

文献信息

• INHIBITORS OF CYSTEINE PROTEASES AND METHODS OF USE THEREOF
  申请人：Siles Rogelio

  公开号：US20090076076A1

  公开（公告）日：2009-03-19

  The present invention relates to semicarbazone or thiosemicarbazone inhibitors of cysteine proteases and methods of using such compounds to prevent and treat protozoan infections such as trypanosomiasis, malaria and leishmaniasis. The compounds also find use in inhibiting cysteine proteases associated with carcinogenesis, including cathepsins B and L.

  本发明涉及半胱氨酸蛋白酶的半胱氨酸脒或硫代半胱氨酸脒抑制剂，以及使用这类化合物预防和治疗原虫感染，如锥虫病、疟疾和利什曼病的方法。这些化合物还可用于抑制与癌变有关的半胱氨酸蛋白酶，包括半胱氨酸蛋白酶B和L。
• Identification and preliminary structure–activity relationships of 1-Indanone derivatives as novel indoleamine-2,3-dioxygenase 1 (IDO1) inhibitors
  作者：Dingding Gao、Yingxia Li

  DOI：10.1016/j.bmc.2017.05.017

  日期：2017.7

  Indoleamine 2,3-dioxygenase 1 (IDO1) plays a vital role in the catabolism of tryptophan along with the kynurenine pathway which is involved in many human diseases including cancer, Alzheimer’s disease, etc. In this study, compound 1 bearing a 1-Indanone scaffold was identified as a novel IDO1 inhibitor by structure-based virtual screening, with moderate to good enzymatic and cellular inhibitory activities

  吲哚胺2,3-双加氧酶1（IDO1）与色氨酸途径一起在色氨酸的分解代谢中起着至关重要的作用，该过程涉及许多人类疾病，包括癌症，阿尔茨海默氏病等。在这项研究中，化合物1带有1-茚满酮支架通过基于结构的虚拟筛选被鉴定为新型IDO1抑制剂，具有中等至良好的酶促和细胞抑制活性。此外，表面等离子体共振分析验证了化合物1和IDO1蛋白之间的直接相互作用。进一步探索了初步SAR，并通过实验和分子对接预测了与IDO1蛋白的结合方式。随后对这些活性化合物的ADME特性进行了计算机分析，结果显示出良好的药代动力学效率。我们认为，这项研究为高效IDO1抑制剂的未来发展做出了巨大贡献，促进了结构多样性。
• Design, synthesis, and biochemical evaluation of novel cruzain inhibitors with potential application in the treatment of Chagas’ disease
  作者：Rogelio Siles、Shen-En Chen、Ming Zhou、Kevin G. Pinney、Mary Lynn Trawick

  DOI：10.1016/j.bmcl.2006.05.041

  日期：2006.8

  A series of compounds bearing tetrahydronaphthalene, benzophenone, propiophenone, and related rigid molecular skeletons functionalized with thiosemicarbazone or unsaturated carbonyl moieties were prepared by chemical synthesis and evaluated for their ability to inhibit the enzyme cruzain. As potential treatment agents for Chagas' disease, three compounds from the group demonstrate potent inhibition of cruzain with IC50 values of 17, 24, and 80 nM, respectively. (c) 2006 Elsevier Ltd. All rights reserved.
• New 1-indanone thiosemicarbazone derivatives active against BVDV
  作者：Liliana M. Finkielsztein、Eliana F. Castro、Lucas E. Fabián、Graciela Y. Moltrasio、Rodolfo H. Campos、Lucía V. Cavallaro、Albertina G. Moglioni

  DOI：10.1016/j.ejmech.2007.10.023

  日期：2008.8

  Identification of new therapeutic agents for the treatment of viral diseases represents an area of active investigation. In an effort to develop new antiviral compounds, a series of 1-indanone thiosemicarbazone derivatives were synthesized. These derivatives were structurally characterized using several spectroscopic techniques and evaluated against bovine viral diarrhoea virus as a surrogate model for hepatitis C virus. Thiosemicarbazone 2m showed potent anti-bovine viral diarrhoea virus activity with a higher selectivity index (SI = 80.29) than that of ribavirin (SI = 11.64). This result determines the potentiality of these thiosemicarbazones as antiviral agents for the treatment of infections caused by other highly related members of Flaviviridae family, as hepatitis C virus. (c) 2007 Elsevier Masson SAS. All rights reserved.
• US8173696B2
  申请人：——

  公开号：US8173696B2

  公开（公告）日：2012-05-08