3-Nitro-1,5,6,7-tetrahydro-2H-cyclopenta[b]pyridin-2-one | 194427-58-2

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 3-Nitro-1,5,6,7-tetrahydro-2H-cyclopenta[b]pyridin-2-one
• 英文别名: 6,7-Dihydro-3-Nitro-5h-Cyclopenta[B]Pyridin-2(1h)-One；3-nitro-5,6-trimethylpyrid-2(1H)-one；3-nitro-1,5,6,7-tetrahydrocyclopenta[b]pyridin-2-one
• CAS: 194427-58-2
• 化学式: C₈H₈N₂O₃
• mdl: MFCD03990527
• 分子量: 180.163
• InChiKey: JJNYQLUGEHFZIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.375
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Nitro-1,5,6,7-tetrahydro-2H-cyclopenta[b]pyridin-2-one 在 镍 盐酸 、 manganese(IV) oxide 、 正丁基锂 、 四甲基乙二胺 、 苄基三乙基氯化铵 、 氢气 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 80.0 ℃ 、202.65 kPa 条件下， 反应 27.0h， 生成 3-Amino-4-(3-methylbenzoyl)-1,5,6,7-tetrahydrocyclopenta[b]pyridin-2-one
  参考文献：
  名称：

  4-Benzyl and 4-Benzoyl-3-dimethylaminopyridin-2(1H)-ones:  In Vitro Evaluation of New C-3-Amino-Substituted and C-5,6-Alkyl-Substituted Analogues against Clinically Important HIV Mutant Strains

  摘要：

  In a program to optimize the anti-HIV activity of the 4-benzyl and 4-benzoyl-3-dimethylaminopyridinones 9 and 10, lead compounds in a new class of highly potent non-nucleoside type inhibitors of HIV-1 reverse transcriptase, modification of the alkyl substitutents at the C-5 and C-6 positions on the pyridinone ring and of the substitutents on the C-3 amino group has been studied. Of the 17 new 5/6-modified analogues prepared, compounds 31b and 32b substituted at C-5 by an extended nonpolar chain containing an ether function and a C-6 methyl group and compound 35 bearing a C-5 ethyl/C-6 hydroxymethyl substituent pattern were selected on the basis of their in vitro activity against wild-type HIV and the three principle mutant strains, K103N, Y181C, and Y188L. When tested further, it was shown that these molecules, and in particular compound 35, are globally more active than 9, 10, and efavirenz against an additional eight single [L100I, K101E, V106A, E138K, V179E, G190A/S, and F227C] and four double HIV mutant strains [L1001 + K103N, K101E + K103N, K103N + Y181C, and F227L + V106A] which are clinically relevant. Concerning modulation of the N-3 substituent, 36 new analogues were prepared. Of these, the N-methyl-N-(2-methoxyethyl)-substituted compounds 40, 42, and 62, as well as the doubly modified compounds 77a and 77b, were selected from the initial screen and were subsequently shown to be active at sub-micromolar concentrations (IC50'S) against all the other mutant strains except K103N + Y181C and F227L + V106A. Two possible, but distinct, modes of binding of these analogues in RT were suggested from molecular modeling studies. The preferred mode of binding for compound 62, corresponding to the predicted "orientation 1", was revealed in the X-ray crystal structure of the compound 62-RT complex.

  DOI：

  10.1021/jm0408621
• 作为产物：
  描述：

  2-氧代-2,5,6,7-四氢-1H-环戊二烯并[b]吡啶-3-甲腈 在 盐酸 、 硫酸 、 硝酸 作用下， 反应 145.0h， 生成 3-Nitro-1,5,6,7-tetrahydro-2H-cyclopenta[b]pyridin-2-one
  参考文献：
  名称：

  4-Benzyl and 4-Benzoyl-3-dimethylaminopyridin-2(1H)-ones:  In Vitro Evaluation of New C-3-Amino-Substituted and C-5,6-Alkyl-Substituted Analogues against Clinically Important HIV Mutant Strains

  摘要：

  In a program to optimize the anti-HIV activity of the 4-benzyl and 4-benzoyl-3-dimethylaminopyridinones 9 and 10, lead compounds in a new class of highly potent non-nucleoside type inhibitors of HIV-1 reverse transcriptase, modification of the alkyl substitutents at the C-5 and C-6 positions on the pyridinone ring and of the substitutents on the C-3 amino group has been studied. Of the 17 new 5/6-modified analogues prepared, compounds 31b and 32b substituted at C-5 by an extended nonpolar chain containing an ether function and a C-6 methyl group and compound 35 bearing a C-5 ethyl/C-6 hydroxymethyl substituent pattern were selected on the basis of their in vitro activity against wild-type HIV and the three principle mutant strains, K103N, Y181C, and Y188L. When tested further, it was shown that these molecules, and in particular compound 35, are globally more active than 9, 10, and efavirenz against an additional eight single [L100I, K101E, V106A, E138K, V179E, G190A/S, and F227C] and four double HIV mutant strains [L1001 + K103N, K101E + K103N, K103N + Y181C, and F227L + V106A] which are clinically relevant. Concerning modulation of the N-3 substituent, 36 new analogues were prepared. Of these, the N-methyl-N-(2-methoxyethyl)-substituted compounds 40, 42, and 62, as well as the doubly modified compounds 77a and 77b, were selected from the initial screen and were subsequently shown to be active at sub-micromolar concentrations (IC50'S) against all the other mutant strains except K103N + Y181C and F227L + V106A. Two possible, but distinct, modes of binding of these analogues in RT were suggested from molecular modeling studies. The preferred mode of binding for compound 62, corresponding to the predicted "orientation 1", was revealed in the X-ray crystal structure of the compound 62-RT complex.

  DOI：

  10.1021/jm0408621

文献信息

• [EN] TRIAZINE DERIVATIVE HAVING EGFR INHIBITORY ACTIVITY, PREPARATION METHOD THEREFOR AND USE THEREOF<br/>[FR] DÉRIVÉ DE TRIAZINE AYANT UNE ACTIVITÉ INHIBITRICE D'EGFR, SON PROCÉDÉ DE PRÉPARATION ET SON UTILISATION<br/>[ZH] 具有EGFR抑制活性的三嗪衍生物及其制备方法和应用
  申请人：ABBISKO THERAPEUTICS CO LTD

  公开号：WO2022033455A1

  公开（公告）日：2022-02-17

  公开了具有EGFR抑制活性的三嗪衍生物及其制备方法和应用。特别地，公开了一种具有式(I)结构的EGFR抑制剂及其制备方法、含有其的药物组合物，以及其制备EGFR抑制剂的用途和其在制备治疗和/或预防至少部分与EGFR外显子20插入、缺失或其他突变相关的癌症、肿瘤或转移性疾病的药物中的用途，特别是在制备治疗和/或预防过度增殖性疾病和诱导细胞死亡障碍疾病的药物中的用途。其中式(I)的各取代基与说明书中的定义相同。
• Synthesis of 3-nitropyrid-2(1H)-ones fromC-nitroacetamide and 1,3-dicarbonyl compounds
  作者：V. P. Kislyi、A. M. Shestopalov、N. D. Kagramanov、V. V. Semenov

  DOI：10.1007/bf02495411

  日期：1997.3

  The reaction of nitroacetamide with 1,3-dicarbonyl compounds afforded 3-nitropyrid-2(1H)-ones. The chemical reactivities of nitroacetamide and nitroacetohydrazide were compared.

  硝基乙酰胺与 1,3-二羰基化合物反应得到 3-硝基吡啶-2(1H)-酮。比较了硝基乙酰胺和硝基乙酰肼的化学反应性。
• [EN] 2,3-DIHYDRO-1H-PYRROLO[3,2-B]PYRIDINE DERIVATIVE, PREPARATION METHOD THEREFOR, AND APPLICATION THEREOF<br/>[FR] DÉRIVÉ DE 2,3-DIHYDRO-1H-PYRROLO[3,2-B]PYRIDINE, SON PROCÉDÉ DE PRÉPARATION ET SON UTILISATION<br/>[ZH] 2,3-二氢-1H-吡咯并[3,2-b]吡啶衍生物、其制备方法和应用
  申请人：ABBISKO THERAPEUTICS CO LTD

  公开号：WO2022116995A1

  公开（公告）日：2022-06-09

  涉及了2,3-二氢-1H-吡咯并[3,2-b]吡啶衍生物、其制备方法和应用。特别地涉及一种具有式(I)结构的EGFR抑制剂及其制备方法、含有其的药物组合物，以及其作为EGFR抑制剂的用途和其在治疗和/或预防至少部分由与EGFR外显子20插入或缺失突变相关的癌症、肿瘤或转移性疾病中的用途，特别是在治疗过度增殖性疾病和诱导细胞死亡障碍疾病中的用途。其中式(I)的各取代基与说明书中的定义相同。
• COMPOUNDS AND COMPOSITIONS FOR TREATING CONDITIONS ASSOCIATED WITH NLRP ACTIVITY
  申请人：Novartis AG

  公开号：EP3880660A1

  公开（公告）日：2021-09-22
• [EN] COMPOUNDS AND COMPOSITIONS FOR TREATING CONDITIONS ASSOCIATED WITH NLRP ACTIVITY<br/>[FR] COMPOSÉS ET COMPOSITIONS DESTINÉS AU TRAITEMENT D'ÉTATS PATHOLOGIQUES ASSOCIÉS À UNE ACTIVITÉ DE NLRP
  申请人：NOVARTIS INFLAMMASOME RES INC

  公开号：WO2020102096A1

  公开（公告）日：2020-05-22

  In one aspect, compounds of Formula AA, or a pharmaceutically acceptable salt thereof, are featured: or a pharmaceutically acceptable salt thereof, wherein the variables shown in Formula A can be as defined anywhere herein.