1,4-Dihydro-1-phenyl-indeno[1,2-c]pyrazole-3-carboxylic acid,ethyl ester | 56456-85-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,4-Dihydro-1-phenyl-indeno[1,2-c]pyrazole-3-carboxylic acid,ethyl ester
• 英文别名: ethyl 1-phenyl-1,4-dihydro-indeno[1,2-c]pyrazole-3-carboxylate；ethyl 1,4-dihydro-1-phenylindeno[1,2-c]pyrazole-3-carboxylate；ethyl 1-phenyl-1,4-dihydroindeno[1,2-c]pyrazole-3-carboxylate；1-phenyl-1,4-dihydro-indeno[1,2-c]pyrazole-3-carboxylic acid ethyl ester；1-Phenyl-1,4-dihydro-indeno[1,2-c]pyrazol-3-carbonsaeure-aethylester；1-Phenyl-3-ethoxycarbonyl-1,4-dihydro-indeno<1.2-c>pyrazol；ethyl 1-phenyl-4H-indeno[1,2-c]pyrazole-3-carboxylate
• CAS: 56456-85-0
• 化学式: C₁₉H₁₆N₂O₂
• 分子量: 304.348
• InChiKey: SMJGVUWXOJJQNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,4-Dihydro-1-phenyl-indeno[1,2-c]pyrazole-3-carboxylic acid,ethyl ester 在 一水合肼 作用下， 以 乙醇 为溶剂， 以87%的产率得到1,4-dihydro-1-phenylindeno[1,2-c]pyrazole-3-carbohydrazide
  参考文献：
  名称：

  新型不对称1,3,4-Oxadiazoles的合成及抗肿瘤评价

  摘要：

  合成了一系列新型的1,3,4-恶二唑类化合物，并在体外肿瘤模型中评估了它们的细胞毒活性。在XTT染料分析中，四种新化合物（2d，2j，2k和2n）显示出生长抑制作用。活性最高的试剂2j对人癌细胞显示出高效力，IC 50值为0.05至1.7μM。初步的SAR相关性表明，恶二唑上链的性质对于体外抗肿瘤效力很重要。化合物2j确定了细胞周期的G 2 / M停滞，并且还激活了强烈的凋亡反应。β-微管蛋白免疫荧光分析表明该化合物2j有效抑制所有癌细胞系中的微管组织，导致异常纺锤体的形成，这并不影响正常人成纤维细胞NB1，Mrc-5和IBR3。由于所有这些原因，化合物2j在化学预防或化学治疗策略中可能是很好的候选者。

  DOI：

  10.1021/acs.jmedchem.6b00468
• 作为产物：
  描述：

  1-茚酮 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 生成 1,4-Dihydro-1-phenyl-indeno[1,2-c]pyrazole-3-carboxylic acid,ethyl ester
  参考文献：
  名称：

  Chromophore-modified bis-benzo[g]indole carboxamides: synthesis and antiproliferative activity of bis-benzo[g]indazole-3-carboxamides and related dimers

  摘要：

  Tricyclic pyrazole dimers that comprise two kinds of CONH-(CH(2))(n)-N(CH(3))-(CH(2))(n)-NHCO bridges to which are linked potential DNA-intercalating groups such as 1H-benzo[g]indazole, 2H-benzo[g]indazole and 1,4-dihydroindeno[1,2-c]pyrazole were designed, synthesized and some of them evaluated in vitro by NCI (Bethesda, USA) against nine types of cancer cells. Compounds 2a, 2f-i and 2o-r demonstrated significant antiproliferative activity, all with GI(50) values in the low micromolar range. Preliminary analysis of the structure-activity relationship for dimers 2 indicated that: (i) in the ground terms (2a and 2k) antitumor activities were strongly related to the type of chromophore, (ii) in contrast, either 1H-benzo[g]indazole- or 1,4-dihydroindeno[1,2-c]pyrazole-dimers when bore a N(1)-aryl group (2g, 2h, 2i, 2o, 2p, 2q and 2r) generally showed a good level of antitumor potency and (iii) for the most representative compounds (pairs of compounds: 2g,2h; 2o,2p and 2q,2r) the length of the bridges did not significantly contribute to the variations in cytotoxicity. Two members of this series, 2f and 2q, were selected and tested in the hollow fiber cell assay to evaluate in a preliminary fashion their in vivo antitumor activity. Finally, viscosity measurement of 2f with poly(dA-dT)(2), confirmed that these promising compounds behaved as typical DNA-intercalating agents.

  DOI：

  10.1016/s0014-827x(03)00131-9

文献信息

• Esters and amides of 4,5-dihydrobenz[g]indazole-3-carboxylic acids and
  申请人：G. D. Searle & Co.

  公开号：US03940418A1

  公开（公告）日：1976-02-24

  Aminoalkyl esters and amides of 4,5-dihydrobenz[g]indazole-3-carboxylic acids and related compounds are described herein. They are useful as anti-ulcer agents, anti-arrhythmic agents, anti-bacterial agents, anti-protozoal agents, anthelmintics, anti-fungal agents, anti-algal agents and anti-inflammatory agents. The compounds are prepared from the appropriate carboxylic acid, alkyl ester, or acid chloride.

  本文描述了4,5-二氢苯并[g]吲唑-3-羧酸的氨基烷基酯和酰胺以及相关化合物。它们可用作抗溃疡药、抗心律失常药、抗菌药、抗原虫药、驱虫药、抗真菌药、抗藻药和抗炎药。这些化合物是从适当的羧酸、烷基酯或酸氯制备而成的。
• Cytotoxicity and Utility of 1-Indanone in the Synthesis of Some New Heterocycles
  作者：Bahira Hegazi、Hanan Ahmed Mohamed、Kamal Mohamed Dawood、Farid Abdel-Rahem Badria

  DOI：10.1248/cpb.58.479

  日期：——

  Benzo[d]imidazole 3 and 1,2,4-triazin-5(2H)-one 6 were prepared by the reaction of starting ethyl (3-hydroxy-1H-inden-2-yl)(oxo)-acetate 2 with o-phenylenediamine and thiosemicarbazide respectively. Reaction of 1,4-dihydro-1-phenylindeno[1,2-c]pyrazole-3-carbohydrazide 8 with phenylisothiocyanate gave thiosemicarbazide 9, and its reaction with chloroacetic acid or phenacylbromides led to the formation of thiazolidinone-4-one 10 or 1,3-thiazoles 12a, b. The reactivity of hydrazide 8 towards fluorinated aldehyde, phthalic anhydride, and hydrazonoyl chlorides 15a, b was studied to give fluorinated hydrazones, imide bis-hydrazones 13—16. The newly synthesized compounds were screened for their cytotoxic activities and compounds 6, 8, 9 and 10 were found the most potentially cytotoxic. The detailed synthesis, spectroscopic and biological data are reported.

  苯并[d]咪唑 3 和 1,2,4-三嗪-5(2H)-酮 6 是通过起始材料乙基 (3-羟基-1H-茚-2-基)(氧)-乙酸酯 2 分别与邻苯二胺和硫脲的反应制备的。1,4-二氢-1-苯基茚[1,2-c]吡唑-3-羟肼 8 与苯异硫氰酸酯的反应生成硫脲 9，随后与氯醋酸或苯基溴化物反应形成噻唑啉-4-酮 10 或 1,3-噻唑 12a, b。还研究了羟肼 8 对氟化醛、邻苯二甲酸酐和肼氟基氯化物 15a, b 的反应，得到了氟化肼酮和酰亚胺双肼 13—16。新合成的化合物进行了细胞毒性活性的筛选，结果显示化合物 6、8、9 和 10 具有较强的细胞毒性。详细的合成、光谱和生物数据已报道。
• Pseudoazulenes. Part VI. Indenopyrazoles and the attempted preparation of an indenoisoxazole
  作者：G. V. Boyd、D. Hewson

  DOI：10.1039/j39680002959

  日期：——

  nitrilimines to indanone-enamines has been established. The pseudoazulenes are protonated on the five-membered carbon ring. Azo-coupling, tropylation, formylation, and condensation with p-dimethylaminobenzaldehyde has been carried out on the diphenyl-compound; the structures of the products and of their conjugate acids are discussed. Attempts to synthesise the ortho-quinonoid 2-methyl-1,3-diphenylindeno[1

  已经制备了2-甲基-1，3-二苯基茚并[2，1- c ]吡唑及其3-乙氧基羰基类似物，其为含有两个稠合的五元环的新型假氮杂腈系统的衍生物。已经确定了将亚硝胺添加到茚满酮-烯胺中的方向。在五元碳环上将假azulenes质子化。已在二苯基化合物上进行了偶氮偶联，对乙酰化，甲酰化和与对二甲基氨基苯甲醛的缩合反应。讨论了产物及其共轭酸的结构。描述了尝试合成邻-醌型2-甲基-1,3-二苯基茚并[1,2- c ]吡唑和苯型2-乙基-3-苯基茚并[1,2- d ]异恶唑的尝试。
• Condensed pyrazole 3-oxo-propanenitrile derivatives
  申请人：Farmitalia Carlo Erba S.r.l.

  公开号：US05424308A1

  公开（公告）日：1995-06-13

  Condensed pyrazole 3-oxo-propanenitrile derivatives of formula (I) ##STR1## wherein X represents a --CH(R.sub.4)-- group, an oxygen atom or a --S(O).sub.n -- group where n is 0, 1 or 2; R.sub.1 represents C.sub.1 -C.sub.6 alkyl, pyridyl or unsubstituted or substituted phenyl; R.sub.2, R.sub.3 and R.sub.4 are as defined herein; and Q represents hydrogen, carboxy, C.sub.2 -C.sub.7 alkoxycarbonyl or a --CON(R.sub.a)R.sub.b group, R.sub.a and R.sub.b being as defined herein; and their pharmaceutically acceptable salts have immunomodulating activity and can be used in particular as immunomodulating agents, e.g. in the treatment of acute and chronic infections of both bacterial and viral origin, alone or in association with antibiotic agents, and in the treatment of neoplastic diseases, alone or in association with antitumoral agents, in mammals.

  化合物(I)的简化吡唑3-氧代丙腈衍生物的化学式如下：##STR1## 其中，X代表--CH(R.sub.4)--基团，氧原子或--S(O).sub.n--基团，其中n为0、1或2；R.sub.1代表C.sub.1-C.sub.6烷基、吡啶基或未取代或取代的苯基；R.sub.2、R.sub.3和R.sub.4如本文所定义；Q代表氢、羧基、C.sub.2-C.sub.7烷氧羰基或--CON(R.sub.a)R.sub.b基团，其中R.sub.a和R.sub.b如本文所定义。这些化合物的药用盐具有免疫调节活性，可用作免疫调节剂，例如在治疗细菌和病毒性的急性和慢性感染时，单独或与抗生素剂联合使用，以及在治疗肿瘤疾病时，单独或与抗肿瘤剂联合使用，适用于哺乳动物。
• Condensed Pyrazole 3-oxo-propanenitrile derivatives and process for their preparation
  申请人：FARMITALIA CARLO ERBA S.r.l.

  公开号：EP0347773A1

  公开（公告）日：1989-12-27

  Condensed pyrazole 3-oxo-propanenitrile derivatives of formula (I) wherein X represents a - CH(R4.)-group, an oxygen atom or a - S(O)n group where n is 0, 1 or 2; R1 represents C1-C6 alkyl, pyridyl or unsubstituted or substituted phenyl; R2, R3 and R4. are as defined herein; and Q represents hydrogen, carboxy, C2-C7 alkoxycarbonyl or a - CON(Ra)Rb group, Ra and Rb being as defined herein; and their pharmaceutically acceptable salts have immunomodulating activity and can be used in particular as immunostimulating agents, e.g. in the treatment of acute and chronic infections of both bacterial and viral origin, alone or in association with antibiotic agents, and in the treatment of neoplastic diseases, alone or in association with antitumoral agents, in mammals.

  式(I)的缩合吡唑-3-氧代丙腈衍生物 其中 X 代表-CH(R4.)-基团、氧原子或-S(O)n 基团（其中 n 为 0、1 或 2）；R1 代表 C1-C6 烷基、吡啶基或未取代或取代苯基；R2、R3 和 R4.如本文所定义；Q 代表氢、羧基、C2-C7 烷氧基羰基或-CON(Ra)Rb 基团，Ra 和 Rb 如本文所定义。例如，单独或与抗生素制剂联合用于治疗哺乳动物的细菌和病毒急性和慢性感染，单独或与抗肿瘤制剂联合用于治疗肿瘤性疾病。