3-(dimethylamino)-1H-naphtho[2,1-b]pyran-1(4H)-one | 35299-76-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 3-(dimethylamino)-1H-naphtho[2,1-b]pyran-1(4H)-one
• 英文别名: 3-(dimethylamino)naphtho[2,1-b]pyran-1(1H)-one；3-dimethylamino-benzo[f]chromen-1-one；1H-NAPHTHO(2,1-b)PYRAN-1-ONE, 3-(DIMETHYLAMINO)-；3-(dimethylamino)benzo[f]chromen-1-one
• CAS: 35299-76-4
• 化学式: C₁₅H₁₃NO₂
• 分子量: 239.274
• InChiKey: GBBYIURNUUGRIA-UHFFFAOYSA-N

物化性质

• 沸点：
  379.6±42.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(dimethylamino)-1H-naphtho[2,1-b]pyran-1(4H)-one 在 三氯氧磷 作用下， 以 甲苯 为溶剂， 反应 3.5h， 生成 1-(2-hydroxynaphthalen-1-yl)-2-(tetrahydropyrimidin-2(1H)-ylidene)ethanone
  参考文献：
  名称：

  Amine Exchange and Unexpected Ring-Opening Reactions of Pyranone Derivatives: Synthesis of 3-Amino-Substituted Oxonaphthopyran-carbaldehydes and Tetrahydropyrimidinethanones as New Potential Oligonucleotide Stabilization Agents

  摘要：

  3-[(3-Aminopropyl)amino]-1-oxo-1H-naphtho[2,1-b]pyran-2-carbaldehyde (10) was synthesized by nucleophilic substitution reaction of 2-(3-dimethylamino)-1-oxo-1H-naphtho[2,1-b]pyran-2-carbaldehyde (9) and the monoprotected propane-1,3-diamine. The reaction with the unprotected reagent led to the unexpected 1-(2-hydroxynaphthalen-1-yl)-2-(tetrahydropyrimidin-2(1H)-ylidene)ethanone (6). Extension of this reaction to chromone 16 gave 1-(2-hydroxy-3-isopropyl-6-methylphenyl) -2- (tetrahydropyrimidin-2(1H)-ylidene)ethanone (7). The X-ray crystal structures of 6 and 7 were also determined.

  DOI：

  10.1002/1522-2675(200206)85:6<1698::aid-hlca1698>3.0.co;2-b
• 作为产物：
  描述：

  N,N,N’,N’-四甲基丙二酰胺 、 2-萘酚 在 三氯氧磷 、 sodium acetate 作用下， 以 氯苯 、 水 为溶剂， 反应 7.0h， 以71%的产率得到3-(dimethylamino)-1H-naphtho[2,1-b]pyran-1(4H)-one
  参考文献：
  名称：

  Synthesis and hybridization properties of the conjugates of oligonucleotides and stabilization agents. Part 3☆

  摘要：

  New compounds having tri- or pentamethylenamine linker functions were synthesized. These derivatives were covalently attached through the 5'-phosphoramide linkage to heptanucleotide pd(CCAAACA). Complementary complexes of the octanucleotide pd(TGTTTGGC) and above oligonucleotide conjugates were tested for their thermodynamic response. The T-m data and thermodynamic parameters for complex formation confirmed the ability of chromone (gamma-pyrone) derivatives to stabilize strongly the 7-mer/8-mer complementary complex. Moreover, benzochromone (naphthopyrane) and, surprisingly, tetrallydropyrimidinethanone derivatives showed the capacity of stabilizing this 7-mer/8-mer complementary complex. The effect of all these compounds on the stability of the oligonucleotide complexes (DeltaG at 37degreesC ranged from - 1.2 to -2.0 kcal/mol) was shown to be comparable to the effect of one nucleotide base pair and similar to the effect (DeltaDeltaG at 37degreesC ranged from -1.5 to -2.0 kcal/mol) found for acridine-oligonucleotide conjugates, which served as a reference in this study. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.12.030

文献信息

• Inhibition of neutrophil O2− production by unsymmetrical methylene derivatives of benzopyrans: their use as potential antiinflammatory agents
  作者：Mauro Mazzei、Ramona Dondero、Enzo Sottofattori、Edon Melloni、Roberto Minafra

  DOI：10.1016/s0223-5234(01)01279-x

  日期：2001.12

  Some unsymmetrical derivatives of benzopyrans 9 were synthesized and tested to verify their PKC inhibitory activity. For this purpose, the Mannich bases of 7-hydroxycoumarins 6 were treated with 2-(dialkylamino)benzopyran-4-ones or 3-(dialkylamino)naphtho[2,1-b]pyran-1-ones 8 in the presence of acetic or propionic anhydride, yielding compounds 9. Human neutrophils stimulated with either PMA and f-MLF

  合成并测试了苯并吡喃9的一些不对称衍生物，以验证其对PKC的抑制活性。为此，在乙酸存在下，用2-（二烷基氨基）苯并吡喃-4-酮或3-（二烷基氨基）萘并[2,1-b]吡喃-1-酮8处理7-羟基香豆素6的曼尼希碱。用丙酸酐或丙酸酐产生化合物9。用PMA和f-MLF刺激的人类嗜中性粒细胞用作细胞模型。化合物9的效率建立在其减少活化的人类嗜中性粒细胞产生O（2）（-）的能力上。在色酮部分的7位带有乙酰氧基的化合物9d和9f似乎有效地抵消了中性粒细胞的活化。
• New polycyclic pyran ring systems
  作者：Mauro Mazzei、Giorgio Roma、Aldo Ermili

  DOI：10.1002/jhet.5570150416

  日期：1978.6

  Reaction of 1-oxo-3-dialkylamino-1H-naphtho[2,1-b]pyrans, 4-hydroxycoumarin and formaldehyde gave rise to the formation of 1-oxo-2-((2-oxo-4′-hydroxy-2′H-1′-benzopyran-3′-yl)-melhyl J-3-dialkylamino-1H-naphtho[2,1-b]pyrans. When these compounds were refluxed in glacial acetic acid, cyclization occurred and 6,8-dioxo-6H,7H,07-,5,15,16-trioxadibenzo[a,j]-naphthacene arose by cleavage of the dialkylamino

  1-氧代-3-二烷基氨基-1 H-萘并[ 2,1- b ]吡喃，4-羟基香豆素和甲醛的反应导致了1-氧代-2-（（2-氧代-4'-羟基-2' ħ -1'-苯并吡喃-3'-基）-melhyl J-3二烷基氨基- 1 H ^ -萘并[2,1- b ]吡喃。当这些化合物在冰醋酸中回流，发生环化和6通过裂解二烷基氨基基团产生了，8-二氧代-6 H，7 H，07-，5,15,16-三恶二苯并[ a，j ]-萘并苯，以类似的方式，从合适的产物开始，许多其他的三氧并萘或合成了氮杂二氧杂萘并衍生物。
• N,N'-DIARYLUREA COMPOUNDS AND N,N'-DIARYLTHIOUREA COMPOUNDS AS INHIBITORS OF TRANSLATION INITIATION
  申请人：Aktas Bertal Huseyin

  公开号：US20120115915A1

  公开（公告）日：2012-05-10

  Compositions and methods for inhibiting translation initiation are provided. Compositions, methods and kits for treating (1) cellular proliferative disorders, (2) non-proliferative, degenerative disorders, (3) viral infections, and/or (4) disorders associated with viral infections, using N,N′-diarylureas and/or N,N′-diarylthiourea compounds are described.

  本文提供了抑制翻译起始的组合物和方法。描述了使用N，N'-二芳基脲和/或N，N'-二芳基硫脲化合物治疗（1）细胞增生性疾病，（2）非增生性退行性疾病，（3）病毒感染和/或（4）与病毒感染相关的疾病的组合物、方法和试剂盒。
• Mazzei, M.; Ermili, A.; Sottofattori, E., Journal of Heterocyclic Chemistry, 1981, vol. 18, p. 863 - 868
  作者：Mazzei, M.、Ermili, A.、Sottofattori, E.、Roma, G.

  DOI：——

  日期：——
• Kaye, Perry T.; Ramaite, Isaiah D.I., South African Journal of Chemistry, 2003, vol. 56, p. 25 - 29
  作者：Kaye, Perry T.、Ramaite, Isaiah D.I.

  DOI：——

  日期：——